Drama Queens - Kal Penn

Episode Date: October 14, 2026

From Hollywood to the White House and back again, Kal Penn has had a front row seat to fame, power, politics and the systems behind them. Kal reveals the wild ride of Harold & Kumar, his decision to put acting on hold for the Obama White House, and what he’s learned about public life along the way. Plus, the twisted real-life saga behind his new movie, "Trust Me, I’m a Doctor."See omnystudio.com/listener for privacy information.

This is an I-Heart podcast. Guaranteed Human. Hi, everyone. It's Sophia. Welcome to Work in Progress. Welcome back to Work in Progress, friends. This week, we sure have a whipsmarty for you. Today's guest has built a career that refuses to fit in one lane, which is something I absolutely love about him,

from Hollywood to the White House. As an actor, a writer, a comedian, and someone who does great political commentary Have you guessed yet? Today's guest is Cal Penn. We actually overlapped on one of my first jobs ever, Van Wilder, back in the early 2000s. He went on to make Harold and Kumar a cult classic hit that then had two more sequels. He took a break from Hollywood to work in the Obama White House on youth outreach and a whole bunch of other interesting stuff you'll hear about today.

In 2021, he published his first memoir, You Can't Be Serious, which pulls, all of his worlds together and reveals so many improbable stories, Hollywood frustrations, and takes some real unexpected turns behind a life that has taken some pretty wild detours. The thing I really appreciate about Cal is he's also a deep nerd. He loves to read. He loves to research. He loves to understand systems. And he has such a fascinating perspective on identity, ambition, and public life that really makes him a person I like to look to for thoughts, opinions, and dialogue. His latest endeavor is a film called Trust Me, I'm a Doctor. And in this movie, he plays a real person, Dr. Sandeep Kapoor, who treated Anna Nicole Smith and whose life was

absolutely upended after she died. Not only is it an interesting story, but it takes place at the height of the early 2000s tabloid era and really explores how fame and media scrutiny and the justice this system can completely reshape a person's life. And after everything Cal's seen from the backlots of Hollywood to the Oval Office in D.C. And back again, I really want to find out what all these experiences have taught him about fame, power, politics, and himself. Let's dive in with Cal Penn. Hello.

Hi. How are you? Good. How are you? I'm good. It's so nice to see you. Good to see you. Well, this is so fun.

And congrats on the movie. I mean, gosh, it's wild. Thank you. It's a weird story. It's a crazy story. It is, but I just, oh, it's great. Okay, we're going to get into that. But before we get into the present and work and all the things,

I actually want to go back to the place that we have in common. Yeah. Take us back to 1980s, New Jersey. What was your childhood like? If we could bump into Cal at eight or nine years old, Do you think you would see yourself in that little boy? Oh, interesting. I've never thought about it that way, like how far we've changed looking backwards.

Yeah, I'm sure there were some things in there. I mean, you're asking 1980s elementary school, New Jersey. I was talking to some friends over the weekend and realized that I think our music teacher in elementary school was a giant stoner and may have been high while teaching. which was fine. She was teaching music and we obviously didn't know. She was lovely. But so I look back and think of all those things. I was like, I wonder how much stuff there was that I just didn't know and didn't register. But I loved growing up in New Jersey. I think, you know, a lot of the, you're right outside New York City. I'm sure plenty of people watching and listening will roll their eyes at New Jersey, but you are wrong. And here's what I mean. Like, okay, you mentioned being eight or nine years old, right?

You take a school trip to, you're learning about dinosaurs in class. You take a school trip to the Museum of Natural History in Manhattan and see all the dinosaurs. Yes. And I remember thinking, obviously this is very cool. But as the years went on, it wasn't until college. I went to school at UCLA, so I went out west. And that was the first time I realized that when other kids learned about dinosaurs, they didn't have the chance to go on a field trip to actually look at dinosaur bones at a world-class museum. So taking all of that for granted, I was thinking about like, okay, yeah, there was that.

There was a lot of children's theater that you could see all over New Jersey or in the city. When we learned about the U.N. in sixth grade, we just went to the U.N. to do a tour. This is a public school, by the way. I didn't go to a private school for anything. So I don't know. I guess when I think back to those days, a lot of that stuff pops up. Yeah. Did you, when you were a little boy, did you know you wanted to be a performer?

A little bit later, I think the like up until 6th grade, I wanted to be an astronaut, which is why you see the space shuttle behind me. And I went to space camp as a kid. I did too. Did you really? Huntsville or Florida? I went in, there's one in Idaho, in California, or at least there was when I was little. Very cool, yeah. And I just loved it.

I have like such a deeply emotional. I don't even want to say a relationship. Just like I'm so emotionally tied to space and the history of all things, NASA. Makes me cry. Yeah. We are on the same boat. It was when I found out that in those days at least, you had to have perfect vision to be a shuttle commander.

The sixth grade me was like, well, that's definitely not going to happen. That's out. This is, I didn't know about LASIC or anything. like that. And I was like, well, now I obviously can't be an astronaut. So I'll just try to play one. Wow. I love that. How did that go over when you told your parents? Oh, that I wanted to be an actor? Yeah. I mean, it didn't go over well. I would imagine like a lot of people. Yeah. Are your parents artists or actors? My dad is a photographer. Okay. So a type of artist. But my parents were like, absolutely, that's not a thing. That you're going to be, no.

You know, very like my mom's family all came to New York and New Jersey from Italy. It was very much the like immigrant energy of like, you could be a doctor, a lawyer, a lawyer, or a doctor. Yeah, yeah. And I was like, okay, but I think I want to be an actor. Totally. Yeah. It wasn't great. We share that in common then because my parents are immigrants.

You know, when they moved to the U.S., it was this post, what they call the post-1965 wave of Asian immigration. where there was a particular immigration law that changed that allowed people from certain Asian countries to come. But only if they had either already had a graduate degree in certain fields or were pursuing one. So in the case of my parents, my dad got into an engineering graduate program in New Jersey, and that's why he got his visa to come here. He and my mom got married in India, but she had a master's in chemistry. So it was like we didn't have enough engineers or doctors or things like, which is why you see that like old school generation of a lot of brown doctors and engineers.

There's nothing genetically inherent about it. It's just the immigration law and what they were screening for. But so because of that, all of their friends and the whole kind of community was very, very much like, no, you're either, to your point, a doctor or an engineer or things that we know that gave us a better life. I talked to my parents about this at length when I wrote a book almost four years ago now. Yeah. And it's a memoir and it's meant to just kind of be funny and light.

And I love like Tina Fey's books and Rain Wilson and Mindy Kaling. And so I wanted to be very similar in tone. But then the subtext is obviously stuff that's a little more serious. And I remember I called my parents when I was turning in my final draft. I was like, hey, I'm looking for a number that I can put in the book that describes how embarrassed you were when I would tell the family friends and the aunties and uncles that like, you know, when I was 15 and cocky that I was going to be a filmmaker instead of a doctor or be an actor instead of an engineer. And they both, this was over Zoom, they were both like embarrassed.

No, we were never embarrassed. We just, we didn't think that this was a career that anybody could have, especially somebody who was from our community. And so we were scared. We weren't embarrassed. And I was like, you know, why do I have to be in my late 30s or early 40s, before I actually ask my parents this and I actually understand that they were scared, not embarrassed.

Like, I'm carrying that around for this long, you know? So when I think back on it, I laugh a lot because it makes sense. I don't have kids, so the things that they've explained to me, I can understand. I can feel as far as having nieces and nephews and being the fun uncle to a lot of my friends' kids. But, man, I can't understand how that must have really been deeply scary to be like, okay, you're going to do what? and how many, how, how, you know, and then explaining to my parents that, like, there is a,

there is a happiness quotient that doesn't come from financial stability. And I don't know if you feel like this, Sophia, but I feel like whenever, whenever we get asked these questions, I acknowledge, like, what a place of privilege I am in today to be able to say, you know, go follow your dreams, et cetera, et cetera. But I remember way back in the day, like in college, working a bunch of odd jobs for those like eight years. It was all like my goal was can I pay my rent through my art period? Can I just, is there a month where the rent and groceries and gas for auditions will will be covered by like a commercial or a couple of days on a TV show that I might be lucky enough to get?

Obviously our stories are different, but I really related to this on multiple levels. but you talk about your book and for our friends at home, if you've been living under a rock and you haven't read the book I'm referring to, Cal's 2021 memoir, called You Can't Be Serious. Perfect title, by the way. Thank you. I also narrate the audiobook for those who prefer that. And they can hear what a wonderful voice you have.

Thank you. We both have voices for podcasts. Yes. But you write in the book really candidly about, you know, the isms you experienced in Hollywood and the racism. and it tracks for me and what you're saying about your parents where their fear probably came from. You know, you say they didn't know a lot of people,

maybe anyone from your community who pursued this kind of a career. And then you talk about how you almost lost the role in Van Wilder, which was also crazy because I was like, we were both in that movie. Totally, yes. Like, what the hell, man? How we have not been hanging out for the last 20 years is so weird to me,

except for at like cool political things because we're fun like that. Exactly. How did that early experience? Like, do you think that that changed how you related to your career or what was possible? Or do you think it made you want to double down and prove that you could continue to do this? I think it was probably both. And that's a great question.

I hadn't thought about it in that context. Like, I think when I decided to pursue the other. I should say that this public high school that I went to also had a magnet program for the performing arts, which is kind of unheard of in public education anymore in the states. There are only a handful of publicly funded arts high schools or arts programs in high schools. And ours had one and I auditioned and got in. And without that, I would not have had the confidence to pursue this professionally. And I'd go on auditions at a lot of times.

I want to be clear, by the way, if you're not watching the video of this, I am laughing about this, which to me is important to do. Yes. It sounds kind of shocking by 2026 standards, especially when you realized this was not that long ago. But the early odds were so toxic. They were so fucking toxic. Yes.

Yes. So it was not uncommon if you looked like me to walk into an audition and know that you were reading for a part that generally was like some kind of brown. Right. Like either. So like let's just. take Van Wilder, for instance, I was, you know, I was reading for the part of an Indian exchange student. And my agent at the time, wonderful woman named Barbara Cameron, who was incidentally

Kirk and Candace Cameron's mom. Oh my God. I know. Crazy. The only agent, by the way, who would, who had responded to years and years of me mailing out headshots and resumes and trying to get somebody to represent me. And she was the only one who called. And she's like, come audition for me. And then that's how we started working together. But she called and was, or her assistant called and was like, there's a great audition for you. It's this movie called Van Wilder. Come to the office so we can talk about it.

I was like, come to the office. This is a big deal. Well, how about you send me the script? We had like nascent email in those days. Send me the script and I'll read it. Tell me the name of the character. Then I'll come into the office and we can talk about it. I'm thinking she's like helping me prep for the audition.

And she keeps saying, honey, just come to the office now. Just come now. It's such a big supporting role. It'd be amazing. there's this guy Ryan Reynolds, he's on the sitcom, two guys, a girl in a pizza place. And everybody knew Tara Reid because American Pie had just come out. And I finally was like, something feels off if you need me to drive to the office. Just send me the script.

I agreed. She agreed to send me the script. I said, what's the name of the character? She was like, okay, you're reading for a character named Taj Mahal. And I hung up on her. And she called back. She's like, I had a feeling you were going to hang up. And I was like, yeah, look.

I didn't graduate from, you know, the UCLA School of Theater, Film, and Television to play a character named after a building. He's named. He doesn't even have a human name. It's crazy. And she was like, listen, read it and let's talk because I think one of the things you'll find is, yes, you are worried about all the stereotypes that are in your head, gal, that they probably exist in this script. But also, if this character was removed from the story, the plot wouldn't advance. from start to finish. And one of the big challenges with stereotypes, I think, regardless,

whether it's any community really that has sort of dealt with them over the years, is that often they seem to exist when writers are lazy. And so the butt of those types of jokes, if they were removed, nothing would really change in terms of the plot, right, of these projects. but there's the rarity where like multiple things are true. Like this could be a stereotype, but also it advances the plot of the film. And I read it and I called a bunch of people. I called some mentors of mine.

What do you think I should do? Should I audition for this? And they all were like, you really, you should because having a supporting lead in a studio, comedy on your resume would really make a big difference. Your agent can pitch you for more things. So I decided to audition. And I remember the final callback. And for people who don't know the story, he's like, yeah, he had like a stereotypical accent and the character had moved from India to go to college in America just because he wanted to get laid.

Now, let's just acknowledge that this was every movie in the early 2000s. That's all they were about. I am not lamenting that one way or the other. I'll also acknowledge because people ask me this all the time and you're right. Yes, there was clearly more than fair amount of misogyny in these movies. Like, this is all, I'm not by telling you. Telling my slice of life story, I'm not trying to ignore all of the other things that people make fun challenging about these movies. Yeah. And to be clear, hindsight is 2020. Like none of this was at the time.

No, exactly. Which speaks to culture at the time. And now we all go, yeah, one of our first movies was, I mean, we were funny and also, ooh. Dude, people ask me this all the time. I do, I do college lectures every now and then. And, uh, and, and, and, and, and, inevitably there will be some very well-meaning student who was born in like 2007 or whatever, who will say, so how much do you regret doing that movie Van Wilder? How embarrassing? Like, how much do you regret it? And I'm just like, first of all, you're fucking welcome.

You're welcome. Okay. I have a career because of that. So A, you're welcome. B, if you're actually asking me in a 2026 lens, do I wish that one of my first movies instead was me jumping out of a helicopter, saving all the good guys and like shooting all the bad guys? Yes, but I don't look like Chris Helmsworth.

And so that's just not going to happen for me. And I'm aware of that, right? Unless I write it now. So it's like, you know, I think the questions that we ask today are with the presumption that we have some sort of a magic wander time machine. And we don't. So instead, I like to talk about these stories and laugh at them because they kind of celebrate both the progress that has been made and also the stuff that we, the work that we still need to do.

Exactly. So I show up at the final audition for Van Wilder. All I know is it's going to be me and another guy auditioning for the part of this Indian exchange student. And we're reading with Ryan Reynolds, who is lovely, by the way, I should say. And I go into the waiting room and the other guy's already there. And I remember thinking before I walked in, I was like, who is it? Like there are a fair amount of brown actors in Hollywood. would. I just, I guess, I guess maybe there's one who I don't know because, you know, you're on

text chains and stuff and share projects and things like that. So I walk in and it is a, it's a white dude and brown face who has already signed in. He's sitting in the waiting room. And I had the following thoughts. I had the following thoughts. My first thought was, oh, shit. Okay. Okay. You've painted your face brown. And, And I'm like, all right. So like, did your agent tell you to paint your face brown? And if you did, like, did this dude do it at home? Or did he do it in the parking lot?

Right? Like before he came up? And then I was like, if he did it at home, did he statistically have a higher likelihood of getting pulled over by the cops? Or did he not? And just all the things going through my head. And then I'm like, ooh, I wonder how his accent is. It's like, is it because he's going to go in there.

He's going to do one, right? Yeah. And then also, I don't know if you relate to this in the same way, but I really, even in those days, sort of was like, my beef is not with this kid. Because we're desperate, man, as actors. You just want to work. You want to get that credit on your resume. And of course, I wasn't, like, thrilled that he was doing this. But I remember just being like, this is a symptom of an institutional challenge and a problem.

And also in my head, I didn't say any of this obviously. I was like, buddy, you can audition for the new WB-CW show where you're playing Shane from Iowa. Yeah. Gets all the girls. I was like, this is mine. Yeah, this is for me. Thank you. I am booking this audition.

And by the way, if I get it, I am going to do it. Like all of the hesitation that I had about whether I should or shouldn't do it if I got it. Like all that went out the window. Gone. fully gone. But then also what was very cool about the audition and then later was like, you know, Ryan asked me to improvise in the audition. He's like, you're very funny.

Can you, you want to just like run the scene? Like, we'll just get the bare bones. And I have, you know, like, I'm a trained actor. I have a background in improv. And that was just such a fun experience. And we kind of continued that a bunch while we were making the movie. So there were things that obviously, you know, I had chat. with the producers and changed and tried to advocate for certain things, you know,

out of a list of 100, maybe you only get 20 of the things that you want. But then the other artistic stuff that you can add was something that I was very grateful for too. But it's crazy. It's crazy to think about now, you know. Yeah. We'll be back in just a minute. But here's a word from our sponsors. The music you love. Your favorite radio stations.

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Always free. Grab the free app. I heart radio. Everywhere you go. Always free. Download the free IHard Radio app today. It's interesting to realize that even in the context of time where there are things you might or do cringe at,

there was still so much good about it. You know, I feel that. It's like, I was playing like the stereotype. hot cheerleader on my first show. And yeah, I made her into something else over the years, but it's like the opportunity was the opportunity. There weren't the opportunities there are now, and that's just what it is.

You know, when I think about the sort of the trajectory of your career, like, you know, studio comedy is a huge leg up for you. Then obviously Harold and Kumar, like, changed everything. What was it about that movie when you read it? Like, did you know at the time it would be huge, or did you feel like it was another step in the right direction in terms of the next job? I read that script and laughed harder than I had laughed at reading a script. And I generally when I read, I don't, I don't emot out loud. Like, I'll laugh, but in my head.

I was laughing out loud, like verbally laughing out loud at the script. And I remember actually So John Hurwitzen Hayden Schlaasberg The two guys who wrote Harold and Kumar Go to White Castle, all the three Harold and Comar movies and a fourth if we get it. Yeah, casual two sequels and maybe another on the way.

So they, I met them before they sold the script. It was a couple months before I think and there was, we had a mutual friend who had a birthday party and that friend was like, hey, and by the way, these were all like, they were assistants or something at the time trying to get their screenwriting crew up and running.

And our friend was like, hey, you should, you should meet John and Hayden. They're good guys. They're big fans of yours from Van Wilder. And you should hear about the script they have. They give me just the bare bones about the story. And I was like, oh, man, this is amazing. I'd love to read it. You're never going to sell it in Hollywood, like to a studio.

But maybe we can all find, like, you know, venture capital was booming in the Bay Area. And like maybe we can find the right people to invest in this. and do a low-budget version. And they looked at me like I was crazy. And they were like, no, no, no, we're going to sell this to a studio. We're making a movie. And I was like, look, let me read it, send it to me. They sent it to me that week.

I read it, like I said, laughed out loud, called them, reiterated that they were not going to sell this to a major studio because it featured two Asian-American men in lead roles in a studio comedy. and I just up until that point, everything I had been told was like, that just doesn't happen or it's not going to happen. And they go, Cal, we are making a movie called Harold and Camargo to White Castle. I understand that you've had friends who have written scripts with performers of color, characters of color, and they were told that somebody would buy it as long as they changed them to make them white characters. We are making Harold and Camargo to White Castle. We are not making David and Jason go to McDonald's.

I was like, okay, that's hilarious. All right. Sure. And then sure enough, a couple weeks later, they sold the script to a company that had a deal with then New Line and I guess Lionsgate Warner Brothers, depending on who bought who at which time. You're right. But it was, and then began this really long process of auditioning because they auditioned people, you know, obviously in New York and L.A., but Vancouver and London and South Africa. So we didn't know, and it didn't have a huge budget when we made it. We thought the script was really funny. The movie comes out and everybody forgets it really tanked at the box office.

It did not do well at all. And it got pulled after its initial whatever, it's a week or two commitment and its run. And then all the calls that I had with like my then manager and agent were like, yeah, don't expect the phone to ring for a while. You know, you guys kind of bombed this movie. And the talk around town is, C, we told you that two Asian American men can't open the studio. comedy, right? And in my head, I was like, I feel like this is not true. I feel like they were underestimating their audience, but I guess they're right. Like, if people didn't show up in the theaters, maybe nobody wants to see a movie like this unless the characters are white or black.

And then two months, I think it's two months later, the movie comes out on HBO and on DVD with zero marketing budget. And fans just found it on their own. Yes. And they bought the DVD, and it was not just the New Yorks and L.A.'s and San Francisco's. It was like Oklahoma and Iowa and the Deep South and people enjoyed this movie and bought it in droves because they just reminded them of friends of theirs and they wanted to go on this kind of funny journey with them. And that was really redemptive, I think, for us, because it was a redemptive because I'm like, see, we can open a movie and have it do well. Yeah. And second, it also just, I mean, I don't know how you feel, but I try to separate like my

art from the politics of things. But it was one of the first feelings I had where I felt redemption that the way that Hollywood then was dumbing down its audience and saying white audiences don't want to see too funny people of color. I just in my heart felt like that was wrong. And to prove that wrong was really great because we all love to laugh. And I'm glad that those movies have a huge fan base of people across the political spectrum. Like the beauty that's left in what we do, that is still there in such a polarizing world, not to make Harold and Kumar more than it should be about. But it's a good feeling to know that, you know,

that that all exists. I don't think it's making it more. I think it's just being aware of, you know, every sort of layer of the systems that we live in for our friends at home. I'm pretty sure the first time we had overlap in the political system was on, was in 08, but I remember being at a specific event with you in 2012. And I don't know. Your whole thing, you know, the fact that you not only were really dedicated to trying to get young people to care about progressive values and, you know, policies that would actually benefit them.

But like, you actually took a break from acting and went and worked in the White House. Like, hello? How did the whole thing happen for you? How did you even do that? I'll give you the kind of, like a semi-abridged. How are we on time? Like the TLDR? I tend to over talk.

Yeah, yeah, yeah, exactly. I'm a talker. Me too. So in 07 and 08, I was on this medical drama house. Olivia Wilde was on house with me at the time. And she knocked on my dressing room door one day. And she goes, hey, I have a plus one to a Barack Obama event. Do you want to come?

And this was October of 2007. So what that means is there were like 12 Democrats and 12 Republicans each running for president. It was the primaries, before the primaries. And nobody really knew Obama. They were like, oh, yeah, he's the young black senator from Illinois. We like his speech from 2004. And that's how I felt, too. And I was like, oh, I'm good, Olivia.

You enjoyed that event. She's like, no, I mean, I have a plus one. I think I think you'd like it. And I was like, yeah, but it's probably like a recruitment event, right? For like, for his campaign. And she's like, yeah. And I was like, yeah, no, I'm good. And she goes, well, I saw you reading his book.

And I was like, yeah, I also read a book about Dick Cheney. Don't need to meet him. You know, it's like I like I like to read. And she kept pushing for a couple of days. And I think like the third or fourth day, she's like, by the way, it's an open bar. I'm like, sold, sold. Done.

Let's go. So we go and it was like 100 people. And it was like, you know, Olivia, I think it was like Justin Timberlake, Usher, there were people like this who were invited. And I figured, okay, if it's going to be 100 artists, basically, somebody is going to ask really good questions about arts policy and public art funding and things like that. So maybe I'll ask a different question. So I went home, and before this event, I was like looking up the Obama website, like, oh, there's a section on climate change.

And I read about, oh, Obama wants to invest in corn to turn into ethanol. And I remembered, this is what a nerd I am. I remember this article that I had read shortly before that in Foreign Affairs magazine, the like thick blue thing that you have to read in college. I still subscribe to it. So I remember there was this article that was like, oh, you know, if we invest too heavily in corn, to turn into biofuels, then it'll drive the price of corn up for people who rely on it in developing countries. And so I'm like, well, then why would he do this? This is a great question to ask. So I had that in the back of my head. Go to this event with Olivia. Obama's making the rounds.

I have like six glasses of wine. Like it is because I'm like, whatever, I'm obviously not signing up to volunteer for this guy's presidential campaign, but there's like free booze and it's a room full of fellow artists. Like, what's not to love? This is great. And Obama comes over and says hi to me and Olivia. And I was like, oh, that's right. My question. Senator, you know, I read on your website that you're investing in corn to turn into ethanol, but isn't that just going to drive up the price of corn for people who rely on it in developing countries? And Obama gives me what now the whole world knows is his, like, cocky smile. And he gives me this really cocky smile. And he goes, oh, well, look, Look, a couple things.

A, I read that article in Foreign Affairs, too. And if you had read my campaign website carefully, you would have seen that I'm proposing investing in corn-based ethanol as a bridge to cellulosic ethanol so that we can one day create biofuels from the grass that grows in our yards. And when you rake your front lawn of leaves, and he just gives me another cocky smile and walks away. And Olivia was like, you just got schooled by Barack Obama. And we both signed up to volunteer for his campaign that night.

You're like, I'm in. I'm in. You got me. I'll do a trip to Iowa for you. So that was kind of the intro. I think a lot of artists at the time in the 0708, the two biggest, they call them surrogates. Yeah. Where you speak on behalf of a candidate. And I think there were a lot of people who did this for Hillary in the early states.

A lot of people who did this for Obama in the early states. And then some of the other candidates, I think the more. I don't want to say fringe, but the less viable candidates had their own sprinkling of people. But so I did that for like a year, over a year, I guess. And then joined the Obama Arts Policy Committee. And by the time the campaign was over, I applied for a job on this like web link, this White House job. Or I was like, I am just curious if I'm even remotely qualified to do this. Like I had gone to grad school for international security.

and I didn't really tell anybody about it. Hello? It was not a full master's. It was like a little, it's a thing you could do online mostly. Okay. I've not done it, but okay. I'm a big nerd.

I wanted to see, like, do any of these things matter? These things that I did because I wanted to. And nobody called. Nobody called me after I submitted my resume and my CV onto this website after Obama won. And I only told my then, my then manager, my like Hollywood manager that I had applied.

And he's like, well, that's crazy, don't you think? I was like, yeah, I'm obviously not getting a White House job. I just wanted to see if I could. If I could. I was like, well, did they say anything? Did you get any feedback? I was like, no, but they must be getting so many applications. Right.

So then right before inauguration, right before Obama's inauguration, I get this phone call that says, hey, will you be part of the inaugural ceremony? There's a concert on the steps of the Lincoln Memorial. and there are artists who are doing many speeches about the state of democracy and then people who are singing. So it was like Bruce Springsteen and Queen Latifah and people like that.

Casual. Very casual. So I got to read a quote, as did like Jack Black and some really funny people I admire. The perk of doing this, the perk of saying yes, was that backstage you got to introduce

your family and friends to the new now first family. And so I brought my parents and my brother and my manager. And, you know, the president said hello and he said, oh, thanks so much for all the work you did. And then Mrs. Obama, who I hadn't really met before,

comes through and she goes, Cal, it's great to meet you. I know all the stuff you did for the campaign. I hope you stay involved. And I assume this is something that Michelle Obama says to everybody. So I said, of course, I definitely plan to. And my manager, who I describe as like every character from the HBO show entourage in one person.

So just like, the former manager says to Michelle Obama, well, you know Cal applied for a job, right? And she's like, what? And I'm like, no, no, no, no. You don't do this. Don't do this. This is not, this is not a Warner Brothers casting office. You don't do this.

And she goes, what do you mean? And he goes, yeah, yeah, he applied for a job. And nobody even called him back. And I am humiliated. And she goes, well, who did you apply with? And I just blurt out, well, I didn't want to bother anybody. So I just put my application on the website. And she looks at me like I was insane. Like you just cold dropped your CV on a website and didn't call anybody. So then she goes,

Hey, Barack, come here. And like, summons the president back over and goes, tell him what you just told me. And I was like, well, sorry, I applied for a job at the White House in case I'm qualified, blah, blah, blah. And he said the same thing. He's like, who did you apply with? And I was like, well, I didn't want to bother anybody. How am I supposed to know who to call? Well, so his point was he looked at me and he goes, why wouldn't you just call somebody? And at that point, I recognized what you know, because you're also an early supporter of a lot of candidates, is that if you start volunteering on a campaign early, you spend time. Like, I had spent time with Barack Obama on the campaign trail. And I knew his senior advisors.

And that's the reason that I worked in 26 states by that point is like, yes, I was good at my job that I was doing. but you do know these people. And so his point was like he was confused whether I was actually serious about that application or not. Because if you don't call anybody, by the way, so the point of that is, so I got a call later that week from somebody who said, look, we're actually looking for, we have one salary to pay, but we're looking for somebody in the public engagement outreach office to cover outreach to young Americans, outreach to the Asian American Pacific Islander community, an outreach to the arts community.

And you taught college, you did youth outreach for us, and you're an artist and understand that community well. Perfect job for you. Perfect job for me. So it just so happened that the timing was right. But the big lesson from that was like in their eyes, they were, you know, like think about it this way, right? And anybody who's listening who has a more traditional job,

or any job, frankly, if you want a job at a particular company, like you're, you know, most actors don't use LinkedIn or anything, but like the way that people use LinkedIn, you're going through your LinkedIn to say, how many degrees of separation you have from somebody who works at a particular company, you're going to make those phone calls. You know that dropping a resume onto an aggregator website is only going to mean that like some AI slop tries to filter through for who has the supposed qualifications.

Right. So you got to call the people. You always have to call humans. And I know you're talking to like young people with jobs who are listening, but I also feel like you're reminding me. I hate doing that. Me too. I hate to call people.

to bother people. I'm like, you know, I'm a fan. I'm here. And that's not the way to get anything done. Nope. This is how I had always felt. I hate it. It really did. It doesn't feel right, I think. Maybe it's a generational thing for us or maybe it's just being too nice. I don't know. But did this, did this lesson and then working in the White House and literally being in charge of outreach, did it change that tendency in you at all? I think it made me a little more pragmatic. for a certain thing, so I'll give you an example. You know, it was funny you're asking me this. I was just telling a friend, and I wondered when I was telling a friend this story.

So I guest hosted two weeks on the Daily Show after Trevor left. Such a dream come true. Loved it. It was awesome. The first week was, I think, when they had like 18 guest hosts or something. And then they whittled it down several months later and had like five or six of us come back to host a second week. And in the middle of that, I remember calling my agents at UTA and thinking to myself, I guess I know this from the Michelle Obama conversation, but really, I've watched enough succession to know that like, you should just ask somebody to go to drinks as an adult human and have a conversation. And if they say no to the drinks, that's fine.

If the drinks don't go well or they go well and it doesn't yield what you want also fine. But like, why not? Why wouldn't you do that? It's like kind of old school, but also if you like people, just do it that way. So I had invited a couple of the execs who were ultimately going to make the daily show decision out to drinks. And I basically made my case where I said, I'd love this job. I am the only guest host who's not a stand-up comedian. Yeah.

So I understand you might have. of qualms about that, but I'm also the only guest host who's worked in the executive branch in politics. So I think there's a value add there too. Anyway, at the end of, at the end of drinks, like the following day, I get this call that's like your guest hosting a second week on the daily show. So I didn't ultimately get the gig. They brought John Stewart back. They're doing this amazing rotating thing with all of their hilarious correspondence. So sure, did it ultimately not go my way? Yes. Did I get two of the most amazing weeks, one being an additional one, because I advocated for myself in a particular way. Yes, but I don't know if that was thanks to Michelle Obama

teaching me a lesson or just watching succession. Right. Maybe a little bit of both. Yeah, a little both. And now a word from our sponsors who make this show possible. The music you love. Your favorite radio stations. Everywhere you go. The podcasts, everyone's talking about. All in one place. And it's free. High heart radio. Whatever you want to hear. Listen anytime. Anywhere. Music, radio. Podcasts. Limited audio. It's on the free IHurt Radio app. Let's go! One app, no subscription.

Always free. Grab the free app. I heart radio. Everywhere you go. Always free. Download the free IHR radio app today. Think about that stuff because you're talking about what sort of advocacy and activism has the most real impact. You obviously had quite an impact working in the White House,

but then you also got to the point where you were ready to step back and go. back into your personal world, into your personal life, you know, writing and making movies and eventually doing your book. And like, how did you decide when it was the right time to fill your cup as an individual after you'd been sort of filling, you know, the social cup for so long? I think, I mean, you know, going off and working, working the above administration was just one of those things where I thought, oh, I, the decision to apply even, I kind of thought, well, I just spent the last like 16 months going to 26 states to tell people that they should support this guy. And now I'm just going to go back to, you know, my fancy TV job, which by the way, loved

and would happily do again, have the job not leave it necessarily. Yes. With me. Yes. Yeah. But I remember thinking like if I am qualified to do this, then maybe there's an opportunity to kind of just see if I can help get the thing done that I promised that this guy would get done because you know you need teams and teams of people to kind of help with that. And I thought it was the right thing at the time. And then when it actually came to fruition, I kind of thought like, oh, this is, you know, what a selfishly, what a historic thing to be part of. And yes, there's no reason to say no. And on your deathbed, are you going to be like, I'm so glad I didn't work for the first black president and get something with health care past,

you know? I'd be like, no, I think I might be like, oh, this TV career was amazing. And I never left it, but I wish maybe I had taken a short sabbatical. I thought I was only going to do a year, and that's what I wanted to do. I wanted to step away from a year and then come right back to acting. And the reason it took almost two and a half is within the first year, I realized almost in those days, you have to just remember almost nothing gets done quickly in politics. That's generally the sign of a healthier democracy. What you're seeing right now is clearly not a healthy democracy, which is why executive action

is so prevalent. But I'm like, oh, right, I've been here almost a year and we still don't have Don't Ask, Don't Tell, repealed. I think we had the ACA. There was no, the Dream Act was still something that was going to be voted on. And I had been working on all of those just as part of the youth, particularly youth outreach components of things. So I stayed until the things that were on that legislative list were going to be done.

I'm like, if they're not done in another year, I'm definitely. leaving regardless because I got to go back to my actual career. I am not working in politics for the rest of my life. So that's when I decided to come back. And amazing first gig, I like, I leave the White House in a couple of weeks later. I'm on the new season of how I met your mother. And I'm like, I'm back with my people. Incredible. So incredible. I love it. Well, and now, you know, fast forward to today, your latest role, which must make your parents so happy. I know it did when I did this. The movie. Trust me, I'm a doctor.

Yeah. You get to play a doctor on screen. I do. But yours is not, you know, total fiction. It's not a created thing. You're portraying the real life doctor whose world kind of got knocked sideways by the death of Anna Nicole Smith. It's a crazy story.

Can you, like, can you give us? Yeah. I don't want to spoil anything, but also I'm like, tell the people what this is all about. Yeah, I won't spoil it, but, um, But yeah, have you played a real person who's still living, by the way? I don't think so. That's got to be wild. It was wild.

This is the first time that I have had the chance to do that. I've played characters from book adaptations and things like that. Obviously played characters based on 10 real people and you do the research that way. But this is the first time there was an actual person. And Anna Nicole Smith, who was a model and reality TV star who tragically passed away in the 2000s, she hurt her doctor, I believe her lawyer and somebody else. There were three people who were on trial in connection with her death, one of whom is her doctor, this guy named Sandeep Kapoor.

And he wrote a book 10 years after this whole ordeal from his perspective about what being put on trial was like. then ends up randomly like kind of selling it to this writer-director-producer pair who turned it into this film. And I remember reading the script a couple years ago being like, isn't this guy in prison? And he is not, right? This just shows you how if you only remember the 15 years ago TMZ People magazine and all the like stuff.

I'm like, oh, yeah, I remember. seeing this with one part of my brain. But you're like guilty. And it's like, wait, no. Oh my God. I'm so sorry. Yeah, exactly. And then there's more to the story.

So I read the script. I'm like, oh, I had no idea. It was this dynamic. I agreed to do it. And then the real Dr. Kapoor was kind enough to let me shadow him. And he's a really quirky, very peculiar in a, in a, like, very loving way guy. And the first thing that I recognized was like I shadowed him. He still has the same practice in L.A.

that he had when Ann Nicole was his patient. But he bought it from an older doctor who was retiring. And she was a patient of the older doctor. So when you buy a medical practice, you're also buying your patient list. So that's how he inherited the patient. But the first thing you notice when you shadow him is that, you know, like, I don't know who your doctors are here,

but if I need to make an appointment with my doctor, I can't really call a human. Right. By the time I get a human, it takes a long time. I can go online and hope that there's something in the next seven weeks where I can get a slot in. Like it's ludicrous, right? This guy, you call him, there's a human who picks up the phone. There are like three receptionists.

And he knows you when you come in. It's like the old 1950s family doctor vibe. So as soon as I saw that, I kind of thought, now I understand how for a cynical American palate, where we can't even reach our doctors or have a conversation with the medical team without it being a whole thing. It seems creepy that you knew your patients so well or that you went to your patient's birthday parties

or things like that. But then you see how he works. I'm like, I guess if I had that relationship with my doctor, like, yeah, you'd get the invite to like the Super Bowl party or you'd get the thing that's like, yeah, come on over. So I think the movie explores a lot of these blurred lines between him and Anna Nicole.

And it was really interesting to play around with that. It's a dark comedy. I almost hesitate saying that because I never want to make light of something that came out of somebody's tragic death. But it was a super interesting thing to work on. I'm glad it's finally coming out. It's really exciting. I also think, you know, I understand the hesitation to describe something as a dark comedy that does revolve around real people when there was a tragedy involved.

But I also think it's an interesting way in. Yeah, for sure. In terms of the container of it, it's like it allows for certain things to come across that I think other traditional devices might not. And so it really does work. And I think because it is, you know, more his story, it makes sense because what a strange, just what a strange thing to kind of get yanked out of your daily life by, you know. And I think about even the era, you know, the early 2000s and the paparazzi and the advent of all those terrible tabloid sites and just, oh, it was just all so gross and terrible, terrible for everybody. And I don't know. Thinking about what public perception felt like then, what it feels like now, you know, now the opinions of you can be sort of swayed online by bot farms people can pay for it.

It's like everything is so nuts. Yep. You know, it's nice to have this opportunity to be reminded to look a little deeper at somebody's story. Definitely. There's a lot of complexity. And there are a lot of flaws there. I mean, the other part that I loved about playing him is he's a flawed character in this story in a way that I think we ultimately will kind of, he'll make you angry. But you'll also empathize because nobody is, you know, nobody's straightforward.

We all make mistakes. Oh, I love it. And I'm thrilled that it. out in the world as well. Before I let you go today, I have to ask you my favorite question that I ask everybody, which is what feels like your work in progress right now? Oh, great question. I'll just be a little vulnerable, I guess.

Pre-COVID, I feel like I was kind of on more of a role creatively in a way that felt grounded for me. I had a show on the air and I was developing a couple of other things. And most of this is also just the marketplace and how people were traditionally buying still up until after COVID and the strikes and all of that. So the one thing that I think is a work in progress is I have a couple of things that I'm pitching and that I'm writing and that I'm working on. I feel a little wobbly, I think, because there are less buyers and there are less kind of people to pitch to. And if it's a crazier idea, you often hear like, let's hold on that for a bit and then come back to it. So there's kind of like that piece of it. But the best part of that work in progress is I've added starting to do stand-up the last few months.

And I'd never done stand-up before. It's insanely scary. So I'm not on like the, it's a trajectory that just looks like this. It's more of a roller coaster where I'm trying to get my sea legs on there and see what's funny and what's not. And like does the R-rated stuff. feel right or is my thing the nerdy political jokes? Like I really don't know. But finding that voice has been like a really fun work in progress too.

Oh my God. That's so exciting. That's one of those things that scares me so much. But I have like, vulnerably for me, I have like a little pin and I'm like someday. Yeah, you should do it. I don't know.

It feels terrifying. Yeah. That's so exciting. Well, I'm super happy for you. Congratulations on all things. Thank you. Thank you. This was such a pleasure. This was awesome. It's great to see you again. This is an IHeart podcast, guaranteed human.