How To Fail With Elizabeth Day - ON EMBARRASSING MOMENTS… With Dan Levy and Phoebe Waller-Bridge

Episode Date: November 3, 2025

Welcome back to this How to Fail episode where we journey through the archive to revisit some of the best bits. This week we’re keeping it light and taking a look at some of the funniest and most en...tertaining embarrassing moments on How to Fail. You’ll hear from Phoebe Waller-Bridge, originally released in July 2018. Phoebe talks about trying to impress Meryl Streep and her body sort of malfunctioned… involving an apple crumble! Then we hear from Dan Levy, from his original episode in January 2024. Dan talks about his birthday cake failure from his childhood and the humiliation at his knee-jerk response. I hope this episode brings some light to your day and reminds us that everyone experiences embarrassment at some point! Listen to Phoebe Waller-Bridge’s full episode of How to Fail here: https://link.chtbl.com/Xr_yQtIZ Listen to Dan Levy’s full episode of How to Fail here: https://play.megaphone.fm/b0cje4y2thgpbbpms2q64w 🔗 LINKS + MENTIONS: Elizabeth’s Substack: https://theelizabethday.substack.com/ Join the How To Fail community: https://howtofail.supportingcast.fm/#content 💌 LOVE THIS EPISODE? Subscribe on Spotify, Apple or wherever you get your podcasts Leave a 5⭐ review – it helps more people discover these stories 👋 Follow How To Fail & Elizabeth: Instagram: @howtofailpod @elizabday TikTok: @howtofailpod @elizabday Website: www.elizabethday.org Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com How to Fail is an Elizabeth Day and Sony Music Entertainment Production. Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts To bring your brand to life in this podcast, email podcastadsales@sonymusic.com Learn more about your ad choices. Visit podcastchoices.com/adchoices Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Starting point is 00:00:16 The substance. This balance is not working. And the naked gun. That was awesome. Now that's a mountain of entertainment. Welcome back to this week's archive episode reflecting on some of the best bits from How to Fail's past. This week we're keeping it light and taking a look at some of the funniest and most entertaining, embarrassing moments from guests on how to fail, starting with the one and only Phoebe Wallerbridge. This is honestly one of the most.
Starting point is 00:01:00 hilarious moments, listening back to Phoebe talking about trying to impress Meryl Streep and her body sort of malfunctioning. And all I need to tell you, because you might have heard it before, is that it involves an apple crumble. I've lost count of the number of times listeners have come up to me at live shows and said, that apple crumble story, and I know immediately what they're talking about. It's one of those anecdotes that gets better every time you hear it. Then Dan Levy talks about a birthday cake failure he remembers vividly from his childhood. and the humiliation he felt at his knee-jerk response to dropping it. I hope this episode brings some light to your day
Starting point is 00:01:37 and reminds you that we all have embarrassing moments, whoever you are. First, it's Phoebe and the Apple Crumble. I was really excited to meet Meryl Streep when I was seeing The Iron Lady. Is she? I was weird with her, though. I go weird around celebrities and always very, in a very individual. your way for each celebrity. I should just not be around them. What did you say to Meryl Street that was weird? Well, Meryl Street was doing the Iron Lady and she was in this prosthetic, sort of whole
Starting point is 00:02:11 body face scenario. The lights were so hot. So whenever she was on set, she didn't, she couldn't really speak in between so much energy was taken up and just like acting through this, you know, mask and everything. So when the light, so she would never say anything in between cuts. And we always knew and she was always like, I'm really sorry, but I just can't, I know I just need to like power down and have a glass of, like, sip some water through this straw. But there was one day when the lights went off, they called cut, and then she just turned around to this room of people and went, you know, in her Margaret Thatcher voice, and just went,
Starting point is 00:02:39 hey, now how's everybody's day? And everyone just freaked out. Everyone just, like, froze in the room, because they were like, oh, my God, everyone at the same time. Like, we were like, vultures, just like, this is our moment to have, to share words with Meryl Street. And so everyone sort of was being very casual. And it was, the scene was like a drinks party or something,
Starting point is 00:02:55 but edging towards her with this kind of wild look their eye and everyone was trying to have some some personal bans with uh with meza so she was just opening the conversation and then it was getting like weirdly competitive and we were like crowding around her but everyone was trying to be very casual and then she started up this conversation about something anyway i tried a joke and it landed and she laughed and she was like oh and everyone else just looked at me with steel and an ashen face and fury and i was like ha ha i won it she's mine she's mine she's mine so she was mine but after that was like she's totally mine she don't you mind. We're going to have a day together. We're going to like nod to each other
Starting point is 00:03:31 respectfully in the corridors. We're going to, we may even like, you know, graduate to a drink at some point. And then at lunchtime, I was sitting at this table with everybody and I was eating this apple crumble and she came down the stairs. She was feeling lively this day, obviously outside of the prosthetic. She came down the stairs and she was walking towards me and I was like, oh my God, oh my God. Like, she's going to come to the table and we're friends now because I was the one that made to laugh and she walked up to the table and she put her hand on my shoulder and she said oh what are you eating i have never answered why i got so excited about the banter with mel that i flung my apple crumble straight into my chest my costume chest and i and i literally squawked my
Starting point is 00:04:17 apple crumble and she went oh and then she went back to her and American accent, which she hadn't done for the whole time. And she went, I wasn't going to take it from you. And I was just holding this awful, like, dripping pudding over my beautiful silk shirt. And I'm just holding it there really tightly not letting it go. I was just like, oh my God, my God, everyone's doing it. I was like, what was that? That was the strangest response.
Starting point is 00:04:42 And then she was like, okay. And then she moved off, and then I had to go and apologize costume thing. So just weird stuff like that. You made her break character. You made Meryl Streep break character. Your first failure relates to a time in second grade, which for UK listeners, is when you're about seven or eight years old? I would think so.
Starting point is 00:05:05 Yeah. It's like kindergarten for a couple years, and then first grade and second grade. So I don't know what that. Yeah. So what happened? I bring this up as a failure because sometimes, you know, there are these snags in our memory where we stick on these moments, and they should have just come and gone. And yet they are as vivid as the day it happened.
Starting point is 00:05:25 And the earliest huge failure for me was it was my birthday, except my birthday's in August. So we, you know, you're very young and you want to celebrate with everybody because everybody who has a birthday during the school year gets to have cake and thing. So my mom made me a cake to bring in right as the school year started in September in Canada. So we did a celebration around my birthday because it's in August. And I was feeling a little embarrassed anyway because it wasn't really my birthday, but it was, anyway. The cake is at the back of the classroom. My teacher says, we have a surprise for the class. I knew what the surprise was.
Starting point is 00:06:07 And she said, Daniel, I'm going to go and get the cake. And I said, no, no, no, I can get the cake. I'll get the cake. Very excited, happy to share with the class. The cake is revealed. The class is excited. Just as I get to the front of the classroom, I trip. and the cake falls out of my hand and onto my shoes and flips sort of cake first onto the
Starting point is 00:06:27 ground. And the class obviously is hysterically laughing. And it is the deepest humiliation I'd felt in my young life. And I looked around and didn't know what to do. And it's that time where you're young and you don't know whether you should cry or laugh. And so my reaction was to sort of, I guess, go completely pale in the face and then reach down and start. to eat the cake off my shoes. I don't know what that impulse was. I think it was kind of panic and deep embarrassment. And it was a moment that I've remembered because, in a way,
Starting point is 00:07:06 I've kind of intellectualized it as like the first exertion of hubris or something. Like I was like, no, no, no, I got the cake. You don't need to get the cake for me. I have it. And I didn't. I was too young. My hands were probably too small. The cake was too heavy. All of those things. And then it just, it was a symbolic thing, I have to say. It's so interesting to me how many people on this podcast do choose moments like that from their early childhood where they embarrass themselves. And I think it's that thing of when you're a child and you're trying to work out who you are in this confusing world and you don't know whether someone has made. making fun of you or is on your side, it can feel quite terrifying.
Starting point is 00:07:54 Yeah. And I, a bit like you, I didn't have the happiest school experience for various reasons. And I wonder what you were like after that as a child at school. What was your school experience? I just, to me, I look back at, I've never liked school. Me neither. Not a single day. And I think part of it had to do with the fact that I wasn't the truest expression of myself.
Starting point is 00:08:18 and I think when you're playing a part, it gets exhausting and you don't like yourself because you're hiding yourself in my particular case. I just wanted to get through it. Because I think in my mind, I thought, once school is done, people will have the maturity to accept me. I think it was toward the end of the last year of my high school experience that I told some friends.
Starting point is 00:08:43 It wasn't a safe space. It's... I mean, it's tough. And I think also when you're the butt of the joke or you are bullied, it makes sense to me that you now write the jokes. Yeah, of course. You want to be in control of when people laugh. Yeah. I didn't think of it that way, but now that you bring it up, it makes sense.
Starting point is 00:09:03 Yeah. It's, and also, yeah, a control of, and also how the jokes are formed. And I think the one thing I learned from both my dad and Catherine O'Hara during the creation of Schitt's Creek was, You can tell very funny jokes about people in celebration of people, but not at their expense. And there's a very fine line between cruel comedy and observational comedy. And I will always lean towards observational comedy. The roast sort of world of it all is its own subculture, which is something I would kill for the self-confidence to endure. I also think that's why shit's worked.
Starting point is 00:09:47 Yes. Because there was a warmth to the comedy and everyone was laughing at themselves as well as everyone else. There was a kind of democracy of comedy across the board. There was no but of the joke. And that will always be something I'm trying to rewrite through my whole life, I think, through anything I do is the kind of reversal of the first chapter of my own life, I guess. Please do follow How to Fail to get new episodes as they have. land on Apple Podcasts, Spotify, Amazon Music, or wherever you get your podcasts, please tell all your friends. This is an Elizabeth Day and Sony Music Entertainment original podcast. Thank you so much
Starting point is 00:10:29 for listening.

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