Not Skinny But Not Fat - Chelsea Handler is More Confident Than Ever

Episode Date: January 13, 2026

Chelsea Handler is finally here fresh off hosting the Critics' Choice Awards for the 4th year in a row! We chat about the big night, any jokes that didn’t make it, who she was rooting for, ...that Timothée thanking Kylie moment and why women are simply better hosts. Period. We go back to her Chelsea Lately days ( my golden star) why it ended, turning 50, and more!!This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.Visit durable.com/notskinny and get started with Durable for free today. When you're ready to publish your website, use code NOTSKINNY for 30% off all plans.Go to LiquidIV.com and get 20% off your first order with code NOTSKINNY at checkout.Take proactive care of your health and head to OPositiv.com/NOTSKINNY at checkout for 25% off your first purchase.Text NOTSKINNY to 64000 to get 20% off all IQBAR products, plus FREE shipping. Message and data rates may apply. Go to quince.com/notskinny for free shipping on your order and 365-day returns. For a limited time, save 40% on your first month at ritual.com/NOTSKINNYProduced by Dear MediaSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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Starting point is 00:00:00 The following podcast is a dear media production. Welcome back to the Not Skinny But Not Fat podcast. I'm your host, Amanda Hirsch, and I still can't believe that I get to chat with some of my favorite stars on my very own podcast where you'll feel like you're just talking shit with your best friends in your living room. Hey guys, happy Tuesday. Welcome to a new episode of Not Skinny Bonafat. This is your girl.
Starting point is 00:00:37 It's Amanda. I really miss you. You haven't felt in my absence. which like you're welcome. Like people take off. I fucking never take off. Like I never take off. I do, how many weeks are there in a year?
Starting point is 00:00:50 52. I do all those. All there is. Just for me, because the industry freaking shuts down from like December 19th till January 5th. Okay.
Starting point is 00:01:01 I just like all those episodes were reported and handed in. So everybody can go on vacation for a very long time. I know it's like annoying to say that I'm happy to be back like to work. like to work and to real life because I understand that I love my job and that's not the case for everybody and I've been there before not loving my job and of course oh my god I've never loved
Starting point is 00:01:21 any job like I was the girl like if my boss stepped out I was leaving I also had no fear I'm like fire me fire me like I'll survive I'll get a different job I was just not and I think because I never liked anything so I was just like never gave it my all until this so I get it if you hate me for saying I was happy to get back to work. It's just like, I'm like, give me an email. Like, give me some news. Give me like a podcast booking. Give me, give me something, something. And it was just so dull. But at the same time, I'm like, okay, there is something nice about like being forced to like not be in the loop because otherwise you're just in it all the time. Another day, another day, another day, you know? And so forced to like, nothing's happening,
Starting point is 00:02:09 girly. Stop checking your email. like everybody's insane Bartz, but you. Actually, I had no desire to be in St. Bartz. And then Bethany Frankel made that reel. It was like it actually sucked to be on influencer island. And I'm just thinking about Andy Cohen calling her the margarita lady. He was like, enough with the TikToks. But I did see that TikTok because she knows how to reel the people in.
Starting point is 00:02:33 It's like why St. Bartz is overrated. And like we're all dying to know because we all saw Nina and fucking Alex Earl and everybody on the same boat with Glenn Powell. And I have to tell you, like, there are things that I look at and I'm like, foam out, like I did not have specific foam
Starting point is 00:02:48 over that boat. Like, I did not want to be on that boat. You know? Like, I did not want to be waking. Like, I'm also not, like, yes, it'd be nice to be on a yacht for a few hours
Starting point is 00:02:57 and have some champagne, but like I'm not like a sleep on the boat girl, which I don't know if they slept on the boat. But also there were like a lot of people, which would like overwhelm me. I love how I think about it so deeply. I'm like, yeah, no, too many people. Anyway, so I'm happy to be.
Starting point is 00:03:11 back. I've missed you. I'm excited for 2026. Like, I'm excited to see what's up, to see what's new, to see what we can do. Who am I? Like, actually, who am I? What else has been going on? There's the mom group drama, which, like, there are moments where I'm like, of course, this is tea. You know, of course that it's tea. And there are moments where I'm like, okay, like, let's calm down. Of course, like, I love Mandy Moore so much. she's a friend of the pod and I'm a huge Hillary Duff fan and Ashley Tisdell's was also on the pod. I always have pod loyalties. So at the beginning, which is so funny, like I know a pop culture expert, but I'm also like naive.
Starting point is 00:03:57 So when people say something, if people are like, this is the truth and I'm like, okay, I believe you. So after Ashley Tisdale's article came out about the toxic mom group, first of all, in the article, she said for people that read the whole thing, And by the way, whatever your theory is, it's not those people. Like, don't go there. It's not true. So I was like, oh, I already seen, like, the photo of all those moms and people assuming it's the Hillary Duff crew. And then I was like, oh, she's saying it's not them.
Starting point is 00:04:25 So it's not them. Okay. This is what how I am. I was like, she's saying it's not them. It also doesn't align for me. Like, Mandy is the nicest person on earth. Like, I was like, no, it can't be. But then obviously I saw, like, they don't, she didn't follow Mandy and Hillary anymore.
Starting point is 00:04:39 And I was like, okay, could it be true? then she put out another statement by her rep saying it's not those girls, like the sleuths got it wrong. And Ashley's not MAGA. She's a registered Democrat, which like, I don't know if that was doing too much. And her husband was posting like, where were you on January 6th? And I'm like, oh, my God, they're doing too much trying to prove all of those things. Like in those situations, you really got to be Kim Kay and just like, sit down. I think, I think. I'm always like, what would Kim Kay do? Anyway, then Matthew Coma, who I'm obsessed with, Hillary Duff's husband, and I've been following him forever. He's the funniest, most underrated person on the planet.
Starting point is 00:05:18 Like, he's just such a fun follow. I almost want to gatekeep him. But he posts real gems and not only his, like, anniversary posts for her, like, everything he posts. He has, like, a relationship with Tiger King Joe. Like, he's hilarious. So he posted this, like, Photoshop photo of, like, his The Cut article being like, when you're the most tone, person on earth, like, nobody wants to be friends with you. So that was, like, confirming.
Starting point is 00:05:41 I'm like, okay, Matthew just fucking confirmed it that it is about them. But, like, he's basically saying Ashley sucks. That's why none of us are friends with her anymore. Then I was like, okay, now I can dive in. You know, he's made it, okay, and he's made it official, kind of. However, since then, it's like, you're either on the side of the internet of, like, they aren't mean girls or you're on the side of the internet that's like Ashley's maga.
Starting point is 00:06:06 and she like bought houses when there were fires and of course they don't want to be friends with her. I'm going to give you a middle road. I'm going to give you the gray area, which I love. Okay. I think, and I said this on Instagram, that Ashley Tisdale wrote this. First of all, she started by writing this as a substack. And I think she got some nice engagement on that substack. I think she got some people in her DMs or whatever being like, I feel you. I like got shunned out by moms and it's such a hard world and your postpartum and whatever. And it's, and difficult. And she was like, oh my God, I'm feeling the love. I'm feeling the community. I'm feeling the sympathy. And I feel good about that. And then she got this offer to do a larger piece for the cut. And she was like, okay, more love, more sympathy, more people understanding
Starting point is 00:06:49 me, more moms, which are like the most engaged audience on the planet reaching out to me and whatever. She felt that. And then it blew up in her fucking face. So on that note, I don't think she meant for it to blow up in her face. I thought she was looking for the sympathy, the love. They're like, it's okay, babe. Like, they suck. You're amazing. I don't think she meant to like expose people or have people. However, then you have the other side of like, okay, but she unfollowed those two. So like you got to put two and two together, honey, right? Right.
Starting point is 00:07:19 I think. Okay. This is, I'm getting to. I'm getting to the fucking point. Okay. Nothing about her article pointed to the fact that they were toxic. And we already know that toxic and like narcissists, those are overused buzzwords that are misused also.
Starting point is 00:07:36 So like nothing in her article made it seem like any of these women she was talking about were toxic. Like that's a very specific word that you can fucking chat GBT, okay? But saying that I was hanging out with these girls and slowly it seemed like they didn't want to hang out with me anymore and that was hurtful to me is okay to say. But that doesn't make these girls toxic or mean. It makes it that they maybe didn't want to hang out with you and maybe you're not the same vibe or maybe you didn't click and they did. And that sucks to feel that way.
Starting point is 00:08:05 and you can make a whole fucking thing about like when you, you know, don't fit in or whatever the fuck. But nothing about the article was pointing to toxic. There was no real story there of like what they did to her aside from kind of not mesh, you know? Like obviously they stayed friends. They're all still friends. And if you're not in the mix, it's like, yeah, they just were not that into you. It's like that movie. Okay.
Starting point is 00:08:31 Because friendships are a lot like relationships. It could go, it's as easy as that. They were just not that. to you. So that's what I think about that whole situation. And I am telling you, Mandy is a nicest person on the planet. And I haven't met Hillary, but obviously I'm a huge fan. And even just putting those things aside, I can just say, like, I've read the article on like a lot of people just reading the headline and seeing the picture of the moms and like assuming whatever. There is not really a story there that's pointing to toxicity. It's more like I wasn't invited
Starting point is 00:09:04 anymore and my feelings were hurt. So that sucks. That sucks. It's a sucky feeling. I agree. It's a sucky feeling. It's kind of like when I write in the mom chat for my son's school and nobody answers. I'm like, are they okay? Like, I'm just wrote a text. I'm like, is it anybody doing this after school and it's like ignoring me? Like, I get it, Ashley. I get it. Anyway, today's guest, such a fucking exciting fucking guest for me. Like this person, has been on my vision board. I'm doing that thing where, like, you don't know who the guest is,
Starting point is 00:09:36 but you know because you write in the title already. Like Chelsea Handler, man, Chelsea lately meant everything to me. It's still if I have, like, general meetings or, you know, if I think about, like, my North Star, it's like, that's what I would want. I would want a Chelsea Lately show. It was everything to me.
Starting point is 00:09:52 I watched it every single time it was on. It was a pinnacle of, like, fucking bad bitch on late night television. And I can't believe that show. It was like off the air. And it wasn't, didn't keep going with her. or than with somebody else. But anyway, and I also read her, like, first book ever,
Starting point is 00:10:08 My Horizontal Life. I am just such a fan of her work and of her career. And she's such a badass. She's like 50 thriving, like living the life. You'll hear in this episode how confident she is in who she is in the decision she makes. And it's admirable and it's inspiring and it's aspirational. So, yeah, enjoy my conversation.
Starting point is 00:10:33 with Chelsea Handler and don't you fucking forget to rate and review this podcast because let me tell you let me tell you what happens you are listening to the pod
Starting point is 00:10:44 you love you like ha ha ha tune in next week I love Amanda but you don't take to the fucking rate and review you know who does somebody that's calling me an industry plan okay that's who's doing it so you need to like
Starting point is 00:10:57 it's so much easier for people to write negative things than positive things so take your positivity take it to the rating and the reviewing. Okay. I appreciate it. Subscribe, follow. I never say to do these things. I'm going to say it now. I have to remind you because you don't do it on your own. Anyway, Chelsea Handler, enjoy you. I feel so not blonde
Starting point is 00:11:17 next to you, you know? Well, I'm really blonde right now. You're really blonde right now. I just had to come. I had to come into town and get my whole thing done. You know what I mean? So I'm fresh. What's your thing? Is it like hair and nails? I eyebrows. I had to get a spray tan, which I abhor. I hate spray tans. I hate the smell. I hate fake tans. But, you know, when I had to host the Critics Choice Awards, I have to look like, you know, I have to have a glow. You looked so good. Thank you. And you didn't change, right?
Starting point is 00:11:39 You had one dress? No, I changed. I changed into a tux at the end of the dress. Oh, right. I love the tugs. Thank you. The power suit, it looked good on you. Yeah, yeah.
Starting point is 00:11:47 I did love the dress too. Thank you. I loved the dress too. And then I wore a different dress for the red carpet. So I had three looks total, but I try not to change too much during those shows. It's really not about me. Well, like, I'm surprised because you're blonde and, like, have a fair complexion. but the beige looks good on you, which my mom always tells me beige doesn't look good on me.
Starting point is 00:12:05 So I'm trying to understand how the beige really looks good on you. Some colors that really don't look good that you wouldn't think look good on people with my skin color somehow look. I can wear orange and yellow and that surprises me. I never knew I could wear those colors. Yeah. No, I did. But I don't, that like Barb is on when I was like, you know, 15 years old. I think I could think I found out I was a spring or a summer.
Starting point is 00:12:27 Oh, they did that? Yeah, they find out what your like color way is. I thought that was a new thing. No, that's an old thing. Really? Huh. But I don't know. I think that's all bullshit anyway.
Starting point is 00:12:37 I mean, you know, you just look good in certain colors. And there's certain colors that no one looks good in, like Chartreuse. Which I don't even know what that is. Yeah, it's hard to spot, actually. It's kind of like a yellowish green. A yellowish green. I had a feeling it was green. Anyway, Chelsea Handler is here, you guys, which I know I look chill right now, but is so exciting for me.
Starting point is 00:12:55 This is exciting. Your book was, my horizontal life was, like, one of my favorite books. Oh, thank you. Remember reading it on the subway and cracking up, like going to high school and just everything, your whole career, everything you've done, Chelsea lately obsessed, like just a huge moment. I love that. Take it in, you guys. Yeah, let's take it in, take it in. And you killed it at the Critics Choice Awards, fourth year in a row.
Starting point is 00:13:16 Yeah, thank you. How was that? Fun. Fun. You just like have fun. I love having fun. I like to make sure my job is fun and that I provide fun for other people and that when you're around me, you're going to have fun. Yeah, everyone, I remember the year you did it.
Starting point is 00:13:32 The first year maybe there were some flops before that. And then you did. And it was like, thank God, right? Yeah. That was the vibe. Or that was the Golden Globes. Oh, that was the Globes? Yeah, because they had Joe Coy and then they had Gerard Carmichael one year.
Starting point is 00:13:47 And that wasn't going well. Oh, okay. And then Nikki came in and she saved the Globes. But I've been doing the critics for four years. And I think Day Diggs did it before me for four years or something like that. So, yeah, I mean, it's just. It's nicer to have women hosting these types of things. Women are just more, it's just we're better at this kind of thing.
Starting point is 00:14:05 Like, in what way? In hosting. Like, I agree. And actually being a host and bringing everyone in and together and setting the tone and the vibe. That's a female thing. You know what I mean? And we're good at that. So women should be hosting award shows.
Starting point is 00:14:17 I totally think that all women, it would be really nice if one of these years, it's only women. Only one for all the awards. So if you do critics, can you not do the other ones? No, you can only really do one. Oh, you can only do one? Yeah. Would you, do you haven't done Oscars? No, I have not.
Starting point is 00:14:31 Would you do? Probably. Yeah. Yeah, I don't see why I wouldn't. Someone came on once to my show and said that these things aren't paid. No. They are? Oh, yeah.
Starting point is 00:14:40 Why did he say that? He was like an actor who like knew his shit. Maybe he didn't know. Maybe he thought you were asking him if he got paid to attend the show. No. Because we were talking about one of the bombs, I can't remember, one of the bad hose. And he was like, well, you know how they would get someone good if they paid them. Mm-hmm.
Starting point is 00:14:57 I get paid. Great. Do you get nervous at all doing that? I get excited. Yeah? Yeah. Nerves are good. So I'm not afraid of nerves. Like, I know if you're nervous, you care. So I want to care. But I'm pretty confident in my capability and my competency. You know what I mean? I know I'm not going to go out there and below it. You know, I'm a comedian. I've been doing this for a long time.
Starting point is 00:15:20 And I know everyone in the room and I know how to handle that kind of situation. And, you know, that's, I like that. Yeah. Is it, but is it, is it? more stressful than going into doing like stand-up. Because this is like Leonardo DiCaprio and like. Yeah, there's a little element of like, oh my God, I'm just going about to go in on all these people, sure. But you get over that pretty quickly.
Starting point is 00:15:40 You do. And I know everybody. You know what I mean? It's not like they don't know who I am. So that makes it easier. Right. If I were to walk into a room of like CEOs and start ripping them apart, that might be different.
Starting point is 00:15:49 Actually, I'd probably enjoy that more, you know, quite frankly. I already have material prepared for that for the people I've never met. But no, it's really fun. and I, nerves used to freak me out when I was like in my 20s and 30s. But one of the greatest things is about getting older and getting mature is like you have so much experience to draw from. So you know what's going to happen. You know like the flurry of emotions that you feel leading up to something and how it's going to shake out.
Starting point is 00:16:15 And you also just start to have confidence in your own ability to nail it. Yeah, like you know that you're going to. Yeah, like I'm reliable. Right. I know I'm reliable. So I'm not that worried about any of the responsibilities I accept. because I'm going to deliver. Do you care about, like,
Starting point is 00:16:29 are you, like, clocking the laughs? Yeah. While you're doing it, you're like, wait, this work, this didn't work. Maybe I'll, like...
Starting point is 00:16:35 I mean, if something isn't as big of a landing as you want it to be, you just keep your, like, you just keep going. Like, it's not like, ugh.
Starting point is 00:16:45 Yeah. You don't freak out. Like, that's very green. That's what's something I would do when I was starting out. I would freak out and then rush through the rest of the set. Yeah.
Starting point is 00:16:52 But you, part of being on stage and commanding an audience is, being in control of that situation. And if a joke doesn't hit as hard as you want, you still stand up tall. Right.
Starting point is 00:17:02 You know, carry on. Like, you're not, like, starting to go in your head. You're not trying to, like, black out. You have to commit to everything you're doing. What was crazy that night that you did, the, the, the Leo and Jeff Bezos thing, which he was cracking up, which was good. Like, he didn't do, he, he responded well, right? Yeah, totally.
Starting point is 00:17:21 Leo's cool. What was another one? Well, I was hitting on Benicio del Toro. Love. I was hitting on Tiana. She heard my pussy popped for her. That was good. What else?
Starting point is 00:17:30 Did we talk about? Wait, what was Benicio's response? He was, he was, he's definitely probably interested in penetration. Wait, you think? Why wouldn't he be? Look at me. First of all, I agree. Is he single?
Starting point is 00:17:40 I think so, but I don't know, actually. I haven't had direct contact with him. Before the joke, we didn't, we didn't do the research to find out. No, no. My job is just to make, you know, sure that I'm making sure that people in the audience that I'm attracted to, know that I'm attracted to them by the time I get done. Because it was worked before. Last year it was Ray Fines.
Starting point is 00:17:58 This year it was Benicio. The year before it was like Robert De Niro and some other, Harrison Ford, I was sitting on them. Yeah. Yeah. But they're both taken and they're way too old for me. Benicio's hot. He can get it. I'd hit that for sure.
Starting point is 00:18:11 Did you watch all the movies? Yes. Okay, so that's part of the homework. That's part of the homework, but I love movies. Yeah. I give you a link with all the movies. So I went up to Whistler. I go to Whistler in the winter.
Starting point is 00:18:23 I have a little ski chalet. And I go up there and I go up there. I literally just cozyed up with my friends. And yeah, and I just watch movies for like two weeks straight. That's fine. I watched them stoned. Then I watched them sober. Then sometimes, you know, one battle after another, I watched like three times.
Starting point is 00:18:39 That movie was just incredible. I know. I started it last night and only could watch half. Yeah. Just because it was my bedtime. Yeah. And it's three hours. What is your bedtime?
Starting point is 00:18:47 Like 11. Oh, okay. What about you? Well, when I'm in New York, I'm here later. But if I'm in L.A., I go to bed around like 9, 30, 10. Oh, that's early. L.A. is a snooest, there's nothing fun happening in L.A. I can vouch for it.
Starting point is 00:18:59 And you party here when you're here? Yeah, I come here and I party. Really? Like, where are you going? Like zero-bond. No, no, no. Oh, you're not kidding. Well, actually, I did go to the bungalow sweets last night or the San Vicente, whatever the hell they're called.
Starting point is 00:19:10 I'm against private clubs. Oh, you're just against them. But my friends were members, so I went and met them. Yeah. I don't subscribe to that kind of nonsense. But you won't go. I'm not paying you for me to come to your restaurant, buddy. Do you think it's true?
Starting point is 00:19:22 Because you were saying at the critics' choice that it says, the tone for the whole award season, like the show, how good it is, but also, like, who's going to win? And you said, get ready to see the people that are going to win tonight for the rest of the season. Yeah. Well, I mean, that's not, no, it's not necessarily true because people win different awards. I honestly think Leo is going to walk away with Best Actor this year at the Oscars. But she did in for, yeah. So you don't think Timmy's going to get it. I don't know. Maybe, but I really would like to see it go to Leo. Leo deserves it. His work, like his catalog of work and his bibliography is just too good.
Starting point is 00:19:55 Yeah. He is the consummate actor. He's the actor of our generation. I fucking love him. You'd hit that. Would I hit that? Yeah. He's cute, but I'm not, you know, I'm too old for Leo.
Starting point is 00:20:05 I'm his age. I mean, you're old. You didn't make that joke, right? No, no. It's an easy. But those jokes have been made. I had to go in a different direction. Yeah, yeah, yeah, yeah.
Starting point is 00:20:16 But you're right. He's like a movie star. You know, he was talking to somebody from the industry. I can I remember who about movie stars. And this person thought that we don't have. them anymore, that that was like the Leo, the Brad, the Clooney that they walk into a room and you're like, do you think that's true that we don't have like real movie stars anymore? I mean, it depends. I think we do. I do think we have movie stars. It's people who are not on social
Starting point is 00:20:38 media, you know, airing their laundry. Like. Like Jacob Allorty, maybe. Yeah, he's a movie star for sure. He's fucking awesome. He's hot. He's talented. Leo's a movie star. There are people that are movie stars. Oh, you think like to be a movie star, you can't be on social media. I think that's a part of it where you're not exposing yourself, like personally so much. Julia Roberts is a movie star. She's a movie star. I mean, there are movie stars. I don't think we're out of movie stars. There's just no mystique left because we know everything that we have there is to know about everybody. So it's become kind of ick. Right. You know what I mean? You know everything. There's not like, it's not like the olden days. So it's not in the same sense, but nothing's like it used to be.
Starting point is 00:21:16 Nothing's like it used to be. Social media has changed all of that. And, you know, definitely for the worst. Yeah. Like if Leonardo Cabrero was posting reels, we would get the ick. Yeah. For sure. Even though his co-star made him do some like TikToks for this movie.
Starting point is 00:21:31 Tiana? No, no, no. The younger one, the one that plays his daughter. Yeah, yeah. So she made him do some tic-tok, which he wasn't like dancing or lip-sinking.
Starting point is 00:21:40 No, but he's cool. He's got a good sense of humor. Yeah, but he sat through them. Yeah, and he's actually quite funny. Yeah. Hey, Leo. Yeah. Just getting more hot for Leo.
Starting point is 00:21:50 Yeah, he's hot. And he was hot in the movie, too. He was hot in the movie. He was. Although, did you see him run? Not a hot run. Not a hot run. I don't know if that was his character running or if that was Leo running.
Starting point is 00:22:02 Because Sean Penn had a weird walk too. Well, Sean Penn had an erection the whole time. So that was his problem. What a humiliating role for Sean Penn I was thinking the whole time. Sean Penn's great though. And you know what also is great about Sean Penn? He doesn't show up to these fucking award shows. And I like that about him.
Starting point is 00:22:16 I know that. He does not give a shit. I get your vibe now, Chelsea. Yeah. You're like, you want the real cool, like not on social. social media, don't care about these things, not trying hard. Like, that's your vibe right now. Yeah, don't try hard.
Starting point is 00:22:32 Don't be thirsty. Don't be, yeah. Thirsty is gross. Yeah. Is it grosser on a guy than it is on a girl? Yeah, yeah, yeah, for sure. Do you think that's like a doublet standard? Not, I don't really care.
Starting point is 00:22:43 You know, there's so many double standards directed at us that if I'm discriminating against men, then I'll so be it. No, I'm with you. I'm with you. What else happened then? Okay, so Timmy thanked Kylie. That was the. Did you feel it in the room?
Starting point is 00:22:56 I just don't understand what that situation is. Is that a real situation? Are they in love? Are they a couple? Well, obviously, he called her my partner, my foundation. I mean, I find her to be amazing that those two are together in a partnership for three years. Yeah. Wow.
Starting point is 00:23:12 So did you, where were you backstage at that moment? I was backstage, yes. And did everyone stop in their tracks? No. I mean, you're in a room in a holding area. Everyone's kind of watching the screens and, you know, I mean, I mean, they've been, there's not much to say about it. Yeah.
Starting point is 00:23:29 Well, the internet did. Yeah. I was like, thank God Timmy won. What did people have to say about it? What was their reaction? Everyone was fainting, dying, losing their mind. Because why? Because he said, I love you.
Starting point is 00:23:42 First of all, it's a big deal to thank someone. Not even every, like, husband thinks their wife or vice versa. Well, that's another reason not to get married, so you don't have to keep fucking thanking that person. But here he is thanking. His girlfriend. Yeah. And he's been doing this before her. So, like, I love the people that are haters that were like, because he said, I couldn't do this without you.
Starting point is 00:24:03 Well, that's ridiculous. Obviously, he could do it without her. That's so stupid. I'm going to do this without you. Yeah, you can. Right. So that's what people were saying. But I think it was just, like, such a, like, whoa, we weren't expecting that.
Starting point is 00:24:15 Like, you're bringing her as your date. Okay. But you're not doing the red carpet together. Like, there's a lot of decisions there. But now you're thanking her for winning the award. But they do. do the carpet together, don't those two? I mean, sometimes they did the orange fit.
Starting point is 00:24:28 Yeah. They did that. Yeah. But that was a big moment. They had security. Do other celebs have security? Some celebs. Like at tables, people come with security, like right behind them?
Starting point is 00:24:39 No, I think she's probably worth so much money that she probably has to go around with security because she could get kidnapped like her sister Kim. Remember when she got robbed in Paris or whatever? I do. I guess that's what's going on. I don't fucking know what's going on with these people, okay? Honestly. What didn't make the cut that was like a good joke? I mean, we put, I don't remember what didn't make the cut,
Starting point is 00:25:01 but if it didn't make the cut, like we put the edgiest stuff in there. Oh, you did. I felt like, oh, do I want to call Kevin Costner a dick? And then I was like, yeah, I guess so. Who cares? That was good. I mean, he kind of is a dick, you know? And I mean, I know him personally, and he's been nothing but sweet to me.
Starting point is 00:25:15 So I felt a little bit like, oh, God, I'm calling him a dick. And I know he gets his feelings hurt too. Right. He takes it personally. Probably the end of that relationship. But then everyone's like, no, you got to do it. You got to do it because he's such a dick. And then, no, nothing.
Starting point is 00:25:29 I mean, I thought of some jokes the next day that I was like, oh, shit. We should have had a tag on that and that. But that's always the case. Because after you, like, see them probably in front of you, like things come to mind. Yeah, like Tiana Taylor, when I told her my pussy, I absolutely pops for her. I should have said, hey, like I told Benicio, it's room 307 at the Ondaz Hotel. Right. Like, I should have tagged that.
Starting point is 00:25:47 But I've missed that boat. But, you know, you win some, you lose some. Was it really a room number? No, I don't stay at the Andaz, just in case anybody's asking. Well, anyway, you did such a good job. Thank you. And are you going to keep hosting it, you think? I mean, we'll see.
Starting point is 00:26:00 It depends what kind of mood I'm in. You know what I mean? Every year I say yes when I feel like it. When you feel like it. We'll be right back after the break. Okay, so you guys already know that I am a complainer when it comes to my period. I do. I do complain a lot so much so that you guys will sometimes diagnose me.
Starting point is 00:26:19 He'll be like, do you have PMD? do you have this? And I'm like, I think I'm just like hormonal. I'm like crampy. I have like mood swings. And that's just like the status quo of my period. Okay. PMS, you guys. It's as simple as PMS. Because if you have a cycle, you already know that you're going to get moodiness. You're going to get breakouts. You're going to get fatigue, irritability, cravings. Like, oh my God, cravings. Like I was eating like an animal. Okay. Before this last period. That's why O positive. and their new flow PMS vitamins are so exciting to me because these are specifically designed to help with PMS symptoms.
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Starting point is 00:32:05 I mean you released your seventh book last year now it's considered last year yeah another New York Times bestseller a night yes that's that's That's crazy. I know. That's amazing. I know. I wish I would have known how successful I would be when I was a little girl. I could have just really chilled out and stopped worrying about so much shit. You were worried. You were worried. You were worried. Yeah, I was worried. When I saw my family, I was like, what the fuck is this shit show? Like, these are my people. I was like, I'm wealthy. I need to be wealthy. I need to be independent. And I need to get the fuck out of New Jersey. And my family was just like, you're six. You know, like, where are you going? And I was like, I'm going somewhere. Watch me. And I'm headed somewhere else. Yes. Far away from this bullshit. Because your dad, I remember from the book was like a used car dealer. I remember. Yeah.
Starting point is 00:32:50 Yeah. He was a hot mess. And my mom was really sweet. My mom was really lovely. But my family was just like not, that was not how I wanted to live my life. And you knew it legit. Right away, I was like, I'm going to make some changes. But did you think like I'm going to be like a CEO or did you know it would be entertainment?
Starting point is 00:33:07 I don't know what age I knew I could go into entertainment, but I was very taken by television and sick on. in the Cosby Show. I loved the Cosby Show. You know, obviously that didn't turn out well for a lot of us. But I love family ties. I loved growing up with like comedy and watching TV. And I definitely related to that the most. I was the most excited about that, you know, as a kid. So I knew I was going to do something. But I just had an imagination of what my life was going to look like as a grown woman. And it wasn't going to be anything like what my family was like. You knew like nice house, nice car. Yeah. I was like, these are not the right cars. These are not the right clothes.
Starting point is 00:33:43 this is not the right house. And I need a housekeeper. Where is she? You know? I was like, where we need a cleaning lady? Like, we need someone who's going to live in. I mean, I had all of the, I wanted a dowry. Like I asked my dad when I was sick and stuff. I had a dowry. He's like, where did you learn that word? And where did you? From a book. I was reading. I was like, I was, when you're the youngest of six kids, you grow up in like five minutes. I mean, I had a vocabulary on me when I was like three years old because I had so many older brothers and sisters and they take me everywhere. So you just kind of grow up and you're mature and you get it. And you pick up things really quickly. Like, you know, you don't miss a trick because you got to get
Starting point is 00:34:19 your attention and you have to get your food. And when you have six kids, you have to fucking know where everybody is at all times. I forgot you were one of six kids. Yeah, it's a lot of people. And you're the youngest. Yeah. So like I had a big, I had big feelings about myself because they made me feel really special. How did your mom have six kids? I don't know. sleep at the fucking wheel. I mean, she just was like, I guess I'll have another baby, you know? I mean, who knows what she was thinking? I don't think she was thinking. She just was like. Pop in the mouth. Yeah. Her and my dad liked to have sex and then get pregnant and then. Well, that's a good thing I got that they like to. Filtful term on all pregnancies, I guess. So you grew up
Starting point is 00:34:58 really fast, realized maybe a little older than six that it is that you're funny, that you could do something like. Yeah, I was very precocious. So my brothers would, I had three older brothers and then the girls are the youngest. So the boys are the oldest. And my brothers would just take me everywhere. And I was really like, you know, I got a lot of attention for being salty and I would go off on people. Like my brothers would be like, go tell that guy he's a fucking loser. And I'd go up and tell him he's a loser.
Starting point is 00:35:22 You know, like I was just like my brothers would like set me up to do crazy things or the night before Halloween on mischief night. You know, they'd have me go play ding-dong ditch and I'd ring the doorbell. And then they'd leave me there, you know? So I'd be running towards the car and they'd pull away and the guy comes out and it's like, hey, little girl. Like they did shit like that to me all. time. So I was very like, you know, that was kind of, I was always kind of that kind of kid. Yeah. I knew how to get in and out of situations quickly and like lie and cheat and steal or
Starting point is 00:35:51 whatever I had to do to like get where I needed to go. So I just was very more, I was older than my age very soon. So were you not as close with your sisters? Like you were more hang out more with your brother? No, I was close with my sisters. Well, my one sister was a little bit of a buzzco because she was kind of a straight-laced, and I didn't have time for that. And she was like, you know, she was very annoying and would always tell on me. And I was... Did you get in trouble or did your parents not care? My parents were just like, they were scared of me a little. They were like, what is this wild? Like, I was wild and I, and my brothers loved it. And they would like crank that out of me.
Starting point is 00:36:26 You know, they would take me to the beach. They wouldn't want to pick up girls so they'd put me in the back of their pickup truck. We'd be on Martha's Vineyard and there would be girls, like these cute hot Swedish girls hitchhiking. And they'd be like, Chelsea, when we get to the beach, you go in the water, act like you're drowning. We're going to come and save you. And then the girls, we're going to take them out, you know, like that. So I'd have to do shit like that all the time. I'd be like, and then my brothers were like, come in the water.
Starting point is 00:36:46 And I'd like, thank God you saved me. Just like to get my brothers late. So like, you know, I just had this kind of childhood that really, it was so fun. I know. I was going to say it sounds fun. It was. Yeah. It was really fun.
Starting point is 00:36:58 We had a lot of great. And wait, but Martha's Vineyard, because I'm remembering it from the book, like you're bringing me back. That's a little bougie, though. Yeah, we didn't have money. It makes it sound like we were well. Right. My dad bought that house for $25,000.
Starting point is 00:37:09 And it was on the water and it was 10 acres. He bought it for $25,000 in 1975. And I think we sold it for like $8, $8 million, $20 years later. No, no, no, sorry, 50 years later, 25. No, I don't know when we sold it years ago. Wow. Yeah. So he was like, before it was what we know it as today.
Starting point is 00:37:30 Before it was Martha's Vineyard, she got that property. But that does sound like a fun childhood. It was. With the lots of siblings and the pranks and the things. Yeah. And we all had a lot of, you know, we all experienced the same level of non-parenting from our parents. My parents were just lame. Like, they wouldn't show up to the school functions.
Starting point is 00:37:50 Like, you know, teachers' night, parents' night. They weren't there? My parents weren't. My dad would come, but you didn't want my dad to come because he would come, like, in a sweater covered in fucking dog hair and, like, rainboot. You know, you're just like, stop. I don't want to be seen with you. And my mom was, she's antisocial.
Starting point is 00:38:04 She was a very Jewish neighborhood that I had Jewish and Italian in Livingston, New Jersey. And my mom was not into that scene because the women were very pushy. And my mom was German and very quiet and demure and not. But Jewish, right? No, not Jewish. My dad was Jewish. We were raised Jewish. My mom was Mormon, actually.
Starting point is 00:38:22 So we kept that, she kept that under wraps as long as she could. Thank God. It was thing because I have kids and I say this is a joke, but I also think it's true. You have kids? I would never have guessed your kids. Really? How many do you have? Why? Because I'm cute and young. Yeah, you don't seem like you have kids.
Starting point is 00:38:36 You don't give off that mom vibe. I love that. Yeah, you should never give off a mom vibe. Nobody wants that. No, that's the best compliment. I mean, I guess it's your mom. Maybe you want it. Right.
Starting point is 00:38:46 Wait. Thank you. How old are they? Five a year and a half. Oh, wow. Look at you. But see, but because of the compliment, I don't know what I want. Oh, kind of.
Starting point is 00:38:54 So because I, like, show up to everything and I'm blah. And I always think as a joke, but I think it's also true that the kids that get neglected end up, like, being, like, fiercer and more independent and having more of a personality. And I'm, like, scared to, like, be a good parent. To be good of a parent. Right. Because, like, those stories of, like, they didn't show up, you know. It's like, I think of that movie.
Starting point is 00:39:19 What was that Sean Penn movie? Like, I am Sam. Like, I just think, like, the smartest kids come from, like, the shittiest growing up situations. Yeah, I mean, it is good. You raise a good point. That's an interesting point. I don't know. I mean, I don't think you could ever love someone too hard or be too reliable on, like,
Starting point is 00:39:38 I think it is a good structure to have parents that show up to your things when you are a kid. Yeah. You kind of need it. I don't look back fondly and think about all the times they forgot to pick me up from fucking Hebrew school in the middle of a snowstorm. And I had to walk three miles and get pneumonia. I don't think about like, oh, my parents really loved me. Yeah. But, yeah, did it build a character?
Starting point is 00:40:00 Yeah. You should have seen me. walked on from Hebrew school one day. We had this janitor that worked at our temple and his name was Isaac. And he had already been through all of my brothers and sisters because they had all gone to Hebrew school too at the same temple. And every Sunday after Hebrew school, there was a lineup where everyone would wait for their parents and their carpools, you know, like, but no one would carpool with my family because my parents never showed up. So I would just go out there and just hope every Sunday that one of them would come, you know? Like, are they here? I know they're not in the line,
Starting point is 00:40:30 but maybe they'll come and pick me up because I'd always have to just wait and wait and they'd be like 20 minutes late, 30 minutes late. And then one day this guy, Isaac, who worked, he came out and he goes, Chelsea, you know, do you want to call your dad? He probably forgot. And I go, you know what?
Starting point is 00:40:44 Fuck these guys. I'm walking home. I'm like, I'm going to teach them a lesson. And I walked three miles home. And it was a snowstorm. And I was not. And I walked in. And my dad was sitting at the kitchen counter,
Starting point is 00:40:55 reading the New York Times. And I just walked in and slammed the door. And I was like, what the fuck is up? with you too. I'm like, I just walked home from from Hebrew school. I'm eight. I'm like, you guys are the worst. And I'm like, and I'm not going to school at all this week because now I have penamonia. And I refuse to speak to them all week and I just took a week off. I'm like, that's what you get. How didn't you make my horizontal life a movie or a show? How didn't I? Yeah, did you? And I don't know, I don't think I did. I feel like it's such a, I could see it. It's a good, it's a good
Starting point is 00:41:30 It's a good animated show, actually. Would it? Yeah. For like actual kids? For a little smart ass, little eight-year-old bitch. She's just yelling at her parents. So to come to our conclusion, I think that it's like, okay, you can't like love them too much and obviously show up.
Starting point is 00:41:44 But there is something in a little bit of maybe tough love to not make them too soft. Well, you can't, yeah. You can't just have everything go your way because then something, the minute something doesn't go your way, you're like, oh, what happened? You know what I mean? But yeah, I mean, it's nice to be. be able to be solution-oriented to a degree. Like, I can take care of myself. Like, you're a survivor. Yeah, I am a survivor. You're a survivor. I started working when I was eight. I mean,
Starting point is 00:42:11 I was like, I have to make my own money. These people were you working. I started my own lemonade stand. Then I started my own vodka lemonade stand because I was like, that's a bigger profit margin. And then I started babysitting. When I was 10 years old, I started babysitting and I lied. I said I was 15. That's wild that we were babysitting at these ages. I was babysitting as a 15-year-old, but I was 10 and I was babysitting for a 14-year-old boy. So he was four years older than me. And I was putting him in time out. Okay. So you weren't with babies. No. Okay. No. I was babysitting somebody. Yeah, someone who was older than me. That's so funny. And so when did you, you went to college or no? Not really. No. Like you tried or, you tried. You tried. It was like, I went to Morris County Community
Starting point is 00:42:47 College or the County College of Morris in Morris Town, New Jersey for about a half a semester. And I just came home one day and looked at my parents. My boyfriend broke up with me. And I was like, I've got nothing left here. I'm like, it's time for me to go to Los Angeles. And my dad was like, let me get a car ready for you. He's like, I'll get you four new tires. Get the fuck out of here. My parents were so over me because I was crazy.
Starting point is 00:43:10 I did so many drugs. And you were living at home? Yeah. And I just was, I was just a nightmare. And I needed to get away from my family to get some space. And then I came back to my family. I needed a break. Like, I didn't like the constraints.
Starting point is 00:43:25 I didn't like childhood. I wanted to be my own person, and I felt like they were restraining me. Did you, were you ever in L.A. before you made that move? Yeah, I had visited L.A. My aunt and uncle lived in L.A. and I had visited L.A. a couple times, and I was like, oh, this is where I'm going to live. Okay, so it wasn't like this like, L.A. No, I just knew that. You knew. I always knew I'd go to L.A. You always knew you'd go. Okay. So then you went at 18? 19 years old. Yeah. And then you arrive and. And I was like, okay, let's start pounding the pavement.
Starting point is 00:43:50 And I just started waitressing. And then I moved in with my aunt and uncle. I lived on their couch. They had nine children. I was their nanny. I drove the kids to school. Is this the Mormon side? Yeah, they're Irish. Because everyone's having so many kids. There's a lot of children in our family.
Starting point is 00:44:04 Lots of people. Lots of, lots of fucking, I guess. Is this what made you so anti-having kids? No, I just thought that seems like it's going to hold me back. Like, just I don't want to deal with it being responsible for another human being. No, that made sense to me. But I'm just now connecting the like, whoa, it's not only that you, it's like a lot of kids all these people have. Yeah, a lot.
Starting point is 00:44:23 Right. Yeah. So I do like kids. I just don't want them. Yeah. I don't want to be responsible for that. Right. It's too much responsibility.
Starting point is 00:44:31 Yeah. I get it. Yeah. I totally get that outlook. I like freedom. So if your friends bring like kids on a trip, does it annoy you? It depends.
Starting point is 00:44:39 What kind of kids? How old are they? What they're a person? Wait, what's baby? What's baby? What's better a baby though? Or like a, you know, sometimes a baby is actually the better. I'm not really interested in babies.
Starting point is 00:44:51 Oh, they need to have like a personality. Yeah. Yeah. Yeah, I want some interaction. Okay, okay, okay. I got you. Yeah, because you're really sweet with like your niece. You post her a lot, right?
Starting point is 00:44:59 Yeah. Do you have a lot of nieces and nephews? I have eight or nine. Eight or nine. Yeah. And are you equally like? No, I favor the girls. Oh, you do?
Starting point is 00:45:08 Totally. Yeah. I mean, it's, they all know it. Like you don't even try with the voice. No, they all know that I'm how I feel. Yeah. I have to favor the girls. Do your sisters or brothers get bad?
Starting point is 00:45:20 No, they are aware of it. I don't lie. I'm just like, listen, this is how it. What it is. Yeah. She's my favorite. Oh, there's one favorite. Well, no, the girls are my favorites.
Starting point is 00:45:29 All the girls are favorites. But that's fun that they get like, you like pamper them. Yeah, I take care of them. That's fun. But do they live in L.A.? No, no one lives in L.A. No one lives in L.A. So they have to like fly out, come visit.
Starting point is 00:45:41 Yeah, yeah. Would you want them to live in L.A.? Are you okay with the distance? I don't need anyone to live in L.A. I barely live in L.A. I'm not even there that much. Really? Yeah, I'm always bouncing around.
Starting point is 00:45:50 I'm on tour. I'm about to start my new tour. So like that's going to keep me away. I have a house in Canada that I spend my winters in because I love to ski. So I don't really spend that much time in L.A. Yeah. I do live there, but I'm not there that often. So no, I'm not looking for anyone to move to L.A. to be closer to me.
Starting point is 00:46:06 Well, okay. In case you were asking. No, because I was wondering, I was like, you're so close with your family, you know. Yeah, sometimes closer than others. Right now, they're on a, they're on a probation. Why? What do they do? Just wives and husbands that I didn't marry that I don't want to deal with.
Starting point is 00:46:20 Oh, wives and husbands. And the spouses of your brothers and sisters, it's like, it's not my problem. And I... So how did it become your problem, though? I just don't want to, like, it didn't become a problem. I just was spending, choosing to spend my vacations with my family and their spouses. And it dawned on me that I didn't marry these people and they're not my spouses. Right.
Starting point is 00:46:40 Those are my sibling spouses. They can deal with them. And I'm going to deal with who I want to deal with. Because they don't want to, like, leave them and go on vacation without the... Yeah. I don't think it's really popular to be like, hey, I'm going away with my sisters and brothers. others and you stay home. I mean, you could do that.
Starting point is 00:46:55 Yeah, I would like to do that. Yeah, you could do just a, or just a girls trip. Yeah, right. Well, my sisters and I are good like that. We can have girls trip. My sister's coming in today. I'm doing Fallon later. She's going to come in.
Starting point is 00:47:06 We're going to the next game together. Yeah. Do you guys have, like, jealousy, like within, so you have two sisters, right? Mm-hmm. Do they, is there, like, one that you're closer with? I'm pretty close to both of them. You get jealous. You're taking her to Fallon.
Starting point is 00:47:20 Does the other one care? Yeah, I like to make them jealous, but I don't know that they, I mean, I don't think it's real jealousy. Oh, they don't really. We're all pretty evenly distributed. Okay. We don't have that. I mean, I'm not jealous. No, I mean, sometimes, yeah, if they're together and I'm not together with them, I'll be like, oh, that sucks.
Starting point is 00:47:34 But no, we're pretty good. I have very good sisters. Yeah. No one's a bitch. We're not drama queens. I mean, I'm the biggest drama queen in the family. And no one wanted your life. No.
Starting point is 00:47:45 No. No one wanted to be in entertainment but you. No, no, no, no. Really? No. That's interesting. Yeah. That's interesting.
Starting point is 00:47:50 Yeah. from like seeing you. No, no. I think that they see what I do and they're like, ugh. Really? Like, ugh. Yeah, like my sister would never want to
Starting point is 00:48:02 walk out on stage in front of a huge group of people. Right. Although she did. She came to my tour one year. I don't know where we were. Maybe Baltimore. And she came out on stage after. And I was like closing the show
Starting point is 00:48:16 and I'm taking pictures with people at the front of the stage and blah, blah, signing stuff. And she came out and I had done a bit about her. And she's like, tell them, I'm the one. I'm the virgin. I'm the virgin. Tell them. And I was like, what are you doing right now? Are you on attention from these people? And so she wanted to see them, but she didn't want any pressure, you know? She wanted everyone to know I was her sister. So I was like, you're funny. I'm like, you wanted that. I'm like, you wanted that attention.
Starting point is 00:48:37 She's like, yeah, I deserve a moment. I'm like, oh, you do? We'll be right back after the break. If you've ever said, I have an idea, but I don't even know where to start. This is for you. durable. Durable. Durable is like having a tiny business assistant in your pocket. You tell it what kind of business you want to start literally in like one sentence and it bills you a full website in under a minute. I'm talking copy, images, layout, all of it. No spiraling, no blank page, no trying to explain some graphic designer, your vision and them just not getting it time and time again. It's not just a website. Durable helps you with invoicing, payments, CRM, marketing, even AI generated content.
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Starting point is 00:54:14 But I also wrote my horizontal life right as that show. was happening. And that book ended up being a real big success for me as a first book, a first time author. Like, first of all, I couldn't believe I was getting a book published. It was such a joke. Wait, so you got the book published before Chelsea Lately? Yeah. Really? I did. Girls behaving badly. Then I got a, I had a couple development deals because I was doing stand-up. So people were giving me like NBC had a development deal for a talk show, not talk show, a sitcom about me, didn't go anywhere. And then I had another development deal with like 20th century or something. And then I got girls behaving badly and then I published my first book. And then when I got Chelsea lately,
Starting point is 00:54:52 I came out with my second book. And then that all kind of happened at the same time. But you're telling you really quickly and it sounds like it all happened in a minute. Like it sounds like, was it that like, oh, I was forming people, I started getting these opportunities or was it? It was like a cascade of like wins and wins. But over the course of about seven years, you know, I don't think I really like hit it, hit it until I was about 33. And that was Chelsea. And that was Chelsea lately. That was when that show blew up. And then my life was like, oh, I'm a famous person now.
Starting point is 00:55:22 I'm a star. Yeah. But stand-up was your thing? Like you were doing stand-up? I started doing stand-up. Oh, you started with doing stand-up, like writing jokes and going out there and everything. Yeah. Oh, wow.
Starting point is 00:55:32 And my horizontal life was amazing because I wrote this book. I used to just tell these stories, like at dinner parties. And somebody was like, you need to write these stories down. They're ridiculous. Like all my one-night stand stories. And so when I sent the book out to, a million different publishers, my manager at the time. And everyone said no, except for this one company, Bloomsbury, which is in the UK. And they were like, we're going to publish this.
Starting point is 00:55:55 It was $35,000 that I, they paid me. $35,000. I was like, 27 years old was my first book deal. And I signed it. And I called my brothers and sisters all went to college. They're like attorneys, one's a CPA, one's a chef. And I called my sister. I'm like, I just got a book deal. And she's like, what? A book about what? And I was like, don't worry about it. Like, I couldn't fucking wait to show, like to have a book published in my family from the only one that didn't go to college. Yeah. Just I knew it was going to drive them all to drink, you know? And that gave me a lot of pleasure. That's why. I didn't realize you wrote it at 27, you said. So then you get Chelsea lately, which is like still to me the pinnacle of like late night. Like,
Starting point is 00:56:36 I just feel like, how did that and how hasn't it happened again? How isn't there a spot for something like that? You know what I mean? Yeah, I don't know. That show should be on the air with somebody else doing it at the very least. But wait, why did it, why did it end? I just was, I was, I was, oh, you, yeah. You were, you? Yeah, I quit. You quit. Yeah, I quit things. Seven years, seven year it. You're over it. I was time to move on. I wanted to do something different. I was bored talking about Lindsay Lohen and Britney Spears and just felt sad at a certain point. It wasn't sad. It was like, it was just not challenging to me. And I'm not, like, I needed to move on and evolve. There were other things I was interested in. I didn't want to just be known as like this catty person that was making fun of people. I wanted to actually learn some stuff and like get into documentaries. And I made a deal with Netflix.
Starting point is 00:57:24 And they kind of let me do whatever the hell I wanted. I traveled the world. I remember that. You know, on their budget. And I liked that. And we filmed everything, you know. But when you made that decision, it was probably a big, like, I mean, I get you being over it after seven years. But how long did you sit with yourself?
Starting point is 00:57:41 Like, wait, I'm giving up. I didn't. You didn't. I don't have a lot of hard times. I'm making decisions. Oh, I'm so jealous. Yeah, no. I just know. Like, it's time. It's time. It's time to change the channel. They try to convince you to say. Yes. Yes. There was lots of money thrown around. And you were like, hell's now. I said, I'm not even interested in the money. It's not about that. I'm done. I want to move on. And then I wanted a year off. I took a year off. I traveled.
Starting point is 00:58:04 Then I told them, you know, Netflix wanted me to do a talk show. And I said, let me just do some documentaries. I wanted to go to Peru and do ayahuasca and film that. So I did that. I went to Russia. I went to Tokyo. We went to India. We filmed it everywhere all over the world. And we had a blast. And then I did my talk show for a couple of years. It wasn't really super successful. These talk shows don't work on these streaming platforms.
Starting point is 00:58:25 I was the first one that did it. What? That was on Netflix? Yeah, Chelsea, it was called. And it was fun, but it wasn't like, I was also, you know, it was a kind of a time. I was turning 40. Trump was elected. I wasn't happy camper about that.
Starting point is 00:58:40 That really threw me off my game, the whole election. And then I kind of got really wrapped up in that. And that kind of led into going into therapy. And then I just needed time off. Like I was like, you know what? I work too much. I just want to be a person and like see what I'm interested in. You know, I didn't want my whole life to be, my whole identity to be like my professional
Starting point is 00:59:01 life. I wanted a life. And you feel like in your 30s, it was all that. Yeah. It was all like work, work, work, work, work. So then I was like, I want to go. I bought a house in Canada. I bought a house in Spain.
Starting point is 00:59:15 I wanted to learn Spanish. Did you? Yeah. I love Spanish, too. It's not perfect, but I can get by. And I wanted to just live a life, like be a real person. And that's what I did. So your 40s were about that, you would say.
Starting point is 00:59:29 Yeah, I mean, I worked because I have to support my lifestyle. But I didn't work in the way that I worked in my 20s and 30s. I just took some time to really get to know myself and to figure out what it is I want and what I'm going after. And what kind of work I am going to do that's going to make me happy. So what did you find that? I found out that I need to just do all of the things I do and not do anything all the time. You know, like my podcast is great
Starting point is 00:59:54 because I get to talk to real people and it's purposeful and I give real advice to people that are looking for real advice. Netflix just bought my podcast so people can watch it on Netflix. I just sold a TV show that I'm going to act in. Woo! Yeah.
Starting point is 01:00:08 I was going to ask you about TV. Yeah, I'm going to do that. So that's exciting. I can't really talk. Oh, we're not talking about it yet. We're not talking about it yet. but it's happening. It's in the works.
Starting point is 01:00:17 I can't make any announcements about that, but that's going to be fun because I've never acted in a... I literally would you ever act? I was thinking about that. I was like, how haven't you done TV in that way? So it's going to happen. Yeah. Hey, I love that.
Starting point is 01:00:31 So I'm really excited about that. And then my stand-up, I just love stand-up. Like, I took six years off from doing stand-up. So coming back to stand-up after that time, I've done three specials in four years. I love it. I have such a newfound respect for it. And for the way I conduct myself at this age and the way that I operate, that it's been like a much more joyful experience, a much more present.
Starting point is 01:00:53 You know, I used to just be shit-faced and be like, oh, I've got three shows tonight. Very loosey-goosey. And of course, I'm always, you know, a little loosey-goosey. But I just kind of recalibrated, you know, I really took some time away from it to understand, do I like this and what do I like about it? And what is my job? And my job is to spread like joy and sunshine. I want people to, like, get the vibe going. I love that there are like two sides of you that like, I feel like people don't see the like super soft side that often.
Starting point is 01:01:23 But like I'm seeing it so often like even in our conversation, you know, even when I'm talking about the kids. Like I was trying to be more like maybe we need to neglect them for them. And you're like, no, never enough love. I'm like, okay. And then now like spread sunshine and joy. Yeah, yeah. I like that. I want people to be inspired also.
Starting point is 01:01:42 But what about the travel, Chelsea? because like you like the planes and the like hopping around. I know, but I'm so used to it. I operate so much better out of a hotel room than I do out of my own house. Sometimes when I'm in my own house, I'm like, this is too much. There's too many things here. I'm going to fuck all of this up. If I'm in a contained hotel room, what could possibly go wrong?
Starting point is 01:02:02 I was just listening, I think, to Ricky Jervais say something about his, do you like him? Yeah. Okay, good. Something about his standup and that he does it like, I think he said like a luxurious tool. Yeah, yeah. I don't fuck around with, no, no, it is. It is. I don't fuck around with Marriott courtyards or any something. I have to, I will not sleep in a city that doesn't have the right hotel.
Starting point is 01:02:24 Is it private? Is it private jet? Sometimes, but not always. No, I fly commercially. Do you take like breaks though? Like, yeah. I'll do like five weekends in a row and then take a week off. Okay. But I do perform Thursday, Friday, Saturday. So it's not like I'm out every night doing shows seven nights a week. Yeah. I know how to do it in a way that I would preserve. my energy and, and, you know, makes me comfortable. Yeah. But, you know, when you do travel as much as I do, you're very used to hotel life. Hotel life, but also like, what about like flights, airports, like all that?
Starting point is 01:02:57 Packing! I don't pack myself. You don't pack yourself. But you know what's in there. They tell you. I see it when I open it. And there's a lot of the same things. So, like, there's a toiletry kit.
Starting point is 01:03:06 Yeah. And at my house in L.A. Is it a stylist or like a assistant? My housekeeper packs me for every trip. but there's a toiletry kit that has everything I need, and there's eight of them. And one of them goes to Whistler, one of them goes to Spain, one of them comes on the road, one of them's in Vegas, like, one of them stays in my hotel in New York that I always stay at. So like I have it dialed.
Starting point is 01:03:26 My life is a dream. And I will never pretend that I am not the most grateful for the way that my life is organized around me because it allows me to just be chill and be myself. I love that for you. I mean, it's really fun to be able to have a career about like, for you. for being myself. Yeah. I don't have to do anything
Starting point is 01:03:45 but be myself. You're not like learning ping pong for seven years. No, but I am really good at ping pong, I want to say. I am. You should challenge Timmy. I don't think that I could beat him
Starting point is 01:03:54 if he's been playing for seven years. I also think that's a long time to be practicing something for a movie. I don't have that kind of commitment. You could pretend. Do you think he took the tour too seriously? He took the press tour too seriously. It seemed so.
Starting point is 01:04:07 Yeah. He seemed pretty serious about winning and getting acknowledged for his great acting. Right. And listen, he's a great actor. Yeah. But it's hard to hear someone talk about how great they are at acting.
Starting point is 01:04:18 I think, because we were talking about Leo before, and I think when I saw him do the press store, that's who I have. That's like my golden star is the Leo's, you know, Leo specifically. And I couldn't, I was like, Leo wouldn't say that. Even though it took him so long to win, right? He didn't win anything until that wrestling with the bear movie. Oh, is that what he won for the bear? The bear, yeah.
Starting point is 01:04:38 Leo wouldn't do that. Leo is a movie star. Yeah. He wouldn't talk. like that. He wouldn't talk like that. I mean, that's new. That's a new... It's kind of like, I haven't heard any actor kind of talk like that. Right. Unless he was being method, which people are speculated. Oh, yeah, right. Right. Is he playing his, he's basically... Right. That would be the only excuse for me if it was that. Right. I was thinking about this today to ask you, even though now that I, like,
Starting point is 01:04:58 got to know you more, I feel like I would know your answer. But how do you deal with, like, competition in this industry, other people doing what you do, maybe getting an opportunity that you want like how do you navigate that? I think when you have first of all jealousy is a completely envy is a completely natural emotion to have and it's really kind of how do you harness that. You have to admit that you feel that way, A, that you are feeling envious or you are feeling jealous. And then you have to realize like you know, you have to digest that. Like how are you going to operate with that feeling? It's totally normal and natural to be envious of people or see people get opportunities in which you had them. But I think with age, you realize, like, what's meant for you doesn't fly by you.
Starting point is 01:05:43 You get what you get. And you don't have to, like, all ships rise with the tide. You know, when women are succeed, we're all succeeding. And blowing out someone else's candle doesn't make yours brighter. You want everyone's candles lit. And you feel that way genuinely inside. Yeah. And even if I don't like someone or I find someone annoying, I remind myself, like, this is somebody who's trying really hard.
Starting point is 01:06:08 and wants to succeed and to be gentle with them and not judge them. Like, I did too. I tried really hard too at a certain point in my life, you know? So to be patient and also to be patient with yourself. It's totally normal to have jealousy. Yeah, because we're always told, like, don't compare. Comparison is a thief of joy, which, like, I agree. If you find yourself doing it, then you can, you know, stop.
Starting point is 01:06:30 But we all do it is the truth. And also don't, don't, but don't act on jealousy. Right. You know, you can have the feeling, but don't go actively. and try to fuck up something for someone else. Like that's... Or like wish for it or like voodoo dough. I hope that person tanks.
Starting point is 01:06:46 I hope they fucking suck. You never wish anything bad upon anybody? I don't actively do that. I find those to be very negative vibes. Okay, the only thing I wish actively is like for certain couples to break up. I think probably a lot of people feel that way. It's like very specific.
Starting point is 01:07:02 That is very specific. But I have a feeling a lot of people feel that way. I'm a woman obsessed. No, but I was being dramatic. today in my head about other things. And I think I texted my sister. I'm suicidal, which you shouldn't say lately. Yeah. But you do, people do.
Starting point is 01:07:16 I've told my friends and my team that I don't have the will to survive at a certain point. I was like, I don't care. I go, guys, I'm not going to kill myself. No one has to worry about that. I'm not killing myself. But if there was like a group euthanasia, I would sign up. Like, I don't have what it takes to continue. I'm exhausted and I'm tired and I'm spent. And that's what I'm at my most depleted. Because I do want to do a group euthanasia at some point. I'm sure you do. I mean, that's just a nicer way to go out.
Starting point is 01:07:41 If everything just falls to shit, I would like to just go to sleep. By the way, I, yeah, or go with everybody. Yeah, and get a group of friends and be like, let's all just take this morphine and call it. So the drug thing. Mm-hmm. Is it because, because you're, like, you talk about, like, smoking pot and, like, doing this up? It's mostly pot, right? No, it's all drugs.
Starting point is 01:08:01 I love all drugs. I love LSD. I love MDMA. I love, I mean, I don't love cocaine and heroin. Right. Those drugs are gross. I mean, I've definitely done them, but I don't do them on the regular. But I'm not, I love drugs.
Starting point is 01:08:13 I think they're a great mind-expander. And they're not for everybody, but they're for me. Did you start later in life? No. Or did you try them when you were growing up? I mean, right now, everything's microdose. So everything to me now is like, it's like, this is the best time for drugs because everything is microdose.
Starting point is 01:08:29 You can get LSD microdose. You get MDMA and microdose. Like, so there's nothing to be scared of because you're not going to get that fucked up anyway. And you probably have like a doctor that like, checks it for you. Oh, I have lots of doctors. Check things for you. Yeah. And make sure it's okay. I have lots of, yeah, I have a whole system. I'm sure you do. I mean, it's like basically breaking bad at my house and Whistler. Yeah, people come over with their MDMA. They have their
Starting point is 01:08:51 capsules. They measure it. We have a drug scale. We're like, okay, let's put 50 milligrams in this. We'll do 150 for this. Da-da-da. And that person gets 100. Like, we prescribe it. Wait, could you be friends and hang out with someone who's like sober? I mean, I try not to. No, stop. For real? Not interested. I have some friends that are sober. What about like drinks but wouldn't do a drug? Yeah, that's okay.
Starting point is 01:09:14 I guess. You're not into it. I'm not going to date a guy, they're going to have to party. Really? Yes. I want a party. I like to get loose. I love you.
Starting point is 01:09:24 And also, this isn't new for you. No. And by the way, I'm 50 years old. Yeah. I'm a perfect shining example of drugs being an enhancement to my life. Yeah. What are you going to say? I'm a mess.
Starting point is 01:09:37 I'm a loser. I don't have it together. I do. But not everyone has your composition. Whatever you're made of. Yeah, no, I have some Hercules, the shit going on into it. I do. You don't have, like, you don't get, like, anxiety.
Starting point is 01:09:48 You don't get, like, hangovers that make you, like, never want to do it again? Sometimes, but not really, no. I don't suffer from that kind of stuff. You wake up and work out. I'm well-trained. I'm a well-oiled machine. You wake up and I work out. Yeah.
Starting point is 01:10:01 You are a machine. I do sometimes have a terrible hangover. Yes, these things happen to me. Yeah. But it's not the euch. It's not the Uge. Y-O-O-J, by the way, if you guys wanted to spell it. That's how you spell U-S.
Starting point is 01:10:13 You did turn 50. Well, 51 in February, right? Yeah, well, let's not get there yet. Well, I know. I like to, I'm with you. Enjoy it till the end. I've been loving this 50 number so much that I don't want to, I just want to stay 50. Yeah.
Starting point is 01:10:24 But I'll go to 51. I'll go. I'll take it. How was that? How was turning 50? How did you take it? It was epic. I had an epic birthday last year.
Starting point is 01:10:32 It was pretty crazy. I had three birthday parties. I, what did I? Oh, my book came out on my birthday. So that was cool. So I was doing press on my birthday, which was a great way to do it. Everywhere I went, somebody sang me, happy birthday. Every show I'd walk on to, they were singing happy birthday.
Starting point is 01:10:46 So that was really fun. And I'm just pretty stoked that this is what 50 is because, I mean, I feel like, you know, definitely hotter than I did when I was 30. I mean, I just want, like, any girl that's listening, like, life keeps getting better and better and better. It's so inspiring. And I'm like, I'm more fit physically than I've ever been. I look better than I've ever been.
Starting point is 01:11:07 I have a lot of help. This isn't all natural. But I'm liking my life. I like my love stories and the men I get to be around and the adventure. I just came back from Antarctica. Like I went on a trip for 10 days to Antarctica. Like I fucking love that I did that. Yeah.
Starting point is 01:11:25 You know, I love, I like the decisions I make and that I'm always up for it. You're like more confident than ever. Yeah. Yeah. Yeah. I feel pretty good about the fact that I don't have to second guess myself ever. that's the thing about aging. Even when you turn like 30,
Starting point is 01:11:42 you get better at the things that you sucked at when you were 20. You know, you like know who you are more. You make decisions for yourself. That's what feels good. And 30s, there's like an air of 30s. There's a period of, am I doing this right?
Starting point is 01:11:55 Am I doing the right thing? Like for me, my 30s were, I was always confident or I had a bravado anyway to make me seem confident, maybe even when I wasn't, you know? but 30s was always like, I wasn't sure. Okay, I know I'm doing well, but like, you know,
Starting point is 01:12:15 not having the confidence of my own conviction necessarily. Like now I just don't ever second-guess myself. That's amazing. Every decision is the right decision. I don't look back and go, what if I did that? It's just whatever decision you make, then you go make a right, then make the right and don't look left. Right.
Starting point is 01:12:32 Then that becomes the right decision. So I'm very decisive. and that's been a good friend to me. And that has gotten only better, like with age, you're saying. Yeah, my instinct, listening to your instinct, listening to your gut, knowing when a person's not good for you, getting away from them. I don't like to learn lessons two, three times. I like to get the message the first time.
Starting point is 01:12:51 So you said you're dating. Is it still the same guy you were like a little gushy over? When was that? Today? No. No, it wasn't today. Maybe it was like a year ago, actually. Oh, no. This is a different guy.
Starting point is 01:13:02 No. It was a guy you were talking about him not having ego. You like that. Oh, yeah. He got cut from the roster. He got cut from the roster. There's a new man in town. There's a new man.
Starting point is 01:13:12 One. So you do like monogamy. Yeah. Yeah. Yeah. Or because I remember you saying you wanted lovers all around the world. I do. I do.
Starting point is 01:13:21 I do. But I'm also open to a little monogamy. Is this guy American? Uh-huh. Yeah, he is. Okay. And he has an ego? He has an ego?
Starting point is 01:13:30 I'm sure he has an ego. Okay. Not like the egoless guy. He's not a guy guy. He's got a lot of good vibrations. He's not like a bro. Okay. Not like that.
Starting point is 01:13:41 Okay. I don't date guys like that. You don't. You date like, well, you did. I mean, not that Joe Coy was a bro, but would you. He's kind of a bro. Would you ever be that public about a relationship again like you were with him? Yeah, I don't really.
Starting point is 01:13:52 Yeah, I don't regret being public with him. I don't care. You guys were like, I know. I know. I was embarrassing. I know, I know. I mean, like, based on what we talked about today, like our icks and, you know, you know. know, stuff like that.
Starting point is 01:14:05 No, that was an echo. Like, not only did I have an Instagram, but you. I know, I know. Listen, believe me, you don't have to tell me, okay? I was just trying to make somebody happy, okay? That was how nice I am. I mean, I shipped, by the way, for the record. If you go back in time, I was all over that, you know, like sad with the breakup,
Starting point is 01:14:25 like I was there. Right. Appreciated people's support of our relationship. It was very sweet. That probably felt good, too. It did. It felt sweet. And I liked it.
Starting point is 01:14:32 And, you know, it was, it was fine for whatever. it was. And then, you know, it wasn't. So every relationship is, like, you don't even make a choice, like, now I'm not going to post anymore, like, who I'm dating. No, I don't care. I don't make, I don't take myself that seriously. Do you know what I mean? Like, I don't have time for, like, secrets or plans or strategies. I'm just doing what I'm doing. If the person is okay with being public, like, I try and respect people's privacy if they're not a public person. But also, I can't guarantee that I'm going to respect your privacy if you date me. Like, it's probably going to be probably going to talk about you at some point. Are you going to do the naked,
Starting point is 01:15:04 ski video this year? Yeah, I think so. I got to figure out where I'm going to shoot it this year, though. You're going to keep it going. Yeah. It's a tradition. I have a great bathing suit for this year, so I got to get that out. See, there's something. She does take seriously. Yeah, yeah, yeah. And the high and mighty tour. Uh-huh. I'm on tour starting February 13th. February 13th. When is New York? New York is being announced in next month. I'm announcing a whole new batch of dates next month. Okay. The tour is on sale. I start in D.C. I'm doing about 60 cities. We're going to add another 60 or 30 cities. I don't know. We're adding a lot of things. Wow. Yeah. So how long is this all going to take probably? Probably. Probably. Because you haven't even announced New York yet. No, no, but I will.
Starting point is 01:15:45 So tickets are on sale. The High and Mighty Tour. This is me trying to get an invite to the New York. Yeah, of course. Come. Yeah, you're welcome to come. That was that. The High and Mighty Tour. So excited. Are you going to be high? I'm going to, yes. Someone's going to be high. And someone's going to be mighty. And it's probably going to be me. Okay. A quick game before I let you go. Overrated underrated or perfectly rated. Okay. Ready for it? Love it.
Starting point is 01:16:07 Barbie, the movie. Perfectly rated. Really? Okay. Yeah, I liked it with that said. The bear. I don't know. I don't watch the bear,
Starting point is 01:16:15 but I've seen it. It made me nervous watching that camera work. It gave me like a little bit of diarrhea. You know what I mean? There's a lot of moving. I like study cams. Cold plunges. Overrated.
Starting point is 01:16:26 Overrated. Oh, you don't do them? No. Okay. Oh, that's cool. Same bars during the holidays. Overrated. Okay.
Starting point is 01:16:33 Tom Brady. Overrated. Chris Jenner's facelift. That's a pretty good facelift. Perfectly, perfectly rated.
Starting point is 01:16:39 Yeah, that's a pretty good facel. Thank you for coming. Thank you. So happy to have you. Thanks for having me. The high and mighty tour. Now you,
Starting point is 01:16:45 not that you need me to sell tickets. Coming to a city near you. Yes. Taylor Swift style. Yeah, right. Taking over the world. Mm-hmm. Exactly.
Starting point is 01:16:53 Thank you. Thank you. Thank you, not skinny, but y'all not fat. Thank you guys so much for listening to this episode of of not skinny but not fat. Follow me on Instagram at
Starting point is 01:17:02 Not skinny, but not fat. Subscribe to the podcast so you don't miss any episodes. Rate the podcast that you love so much on Apple Podcasts and write a little review. If you tell me you did, I'll give you a big virtual smoochoo. Thank you guys so much for listening and I'll see you next Tuesday. Please note that this episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct or indirect financial interest in products or services referred to in this episode.

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