ALEX BLUMBERG: From Gimlet, I’m Alex Blumberg and this is Without Fail, the show where I talk with artists, athletes, entrepreneurs, visionaries of all kinds, about their successes and their failures, and what they’ve learned from both.

Today on the show, we’re doing something we’ve never done before on Without Fail. Instead of just me hosting the show, I’m going to be sharing the stage, with another host, Jonathan Goldstein, the host of another Gimlet podcast called Heavyweight, in which Jonathan helps people revisit difficult moments from their past. 

Jonathan and I go way back - we both worked at This American Life well before Gimlet even existed...when we started Gimlet, he came over and developed Heavyweight here. But this was the first time we’d ever sat down to do a big long interview with someone famous together. So before our guest arrived, I checked in with Jonathan, to see how he’s feeling...

ALEX BLUMBERG: Hello.

JONATHAN GOLDSTEIN: Hi.

ALEX BLUMBERG: Hi.

JONATHAN GOLDSTEIN: Sorry. I'm just having a bite of apple to kind of relax me, you know? Makes me sound more casual.

ALEX BLUMBERG: How are you feeling?

JONATHAN GOLDSTEIN: Um, good. How are you feeling? I’m a little antsy. I think this might be the only formal structured interview I've ever done in my life...

ALEX BLUMBERG: Really?

JONATHAN GOLDSTEIN: ...that can't be -- yeah. I think so. [pause] You think it's a bad idea? It's not too late to take me out.

ALEX BLUMBERG: The reason I would never do that, the reason I’m co-hosting today’s show with Jonathan in the first place, is that he is a huge fan of today’s guest: Nick Kroll — a comedian, writer and actor, who’s been in basically every funny show you’ve ever seen on TV... Parks and Recreation, The League, Community, Portlandia, Kroll Show, the list goes on and on. He’s been in a bunch of movies as well.

He’s best known for playing these ridiculous, over-the-top characters. And he has a ton of them. There’s Bobby Bottleservice, a self-proclaimed “jack of all cards”...

BOBBY BOTTLESERVICE: In a manager of speaking, you could say Bobby Bottleservice, has had an amazing year. Directing, producing, music, producing, gigolo... 

ALEX BLUMBERG: Liz G from the PR firm PubLizity…

LIZ G: There were so many ameeezing guests at the red carpet! A guy from pawnsylvania came...

ALEX BLUMBERG: And Gil Faizon, an elderly prankster from the Upper West Side of Manhattan…

GIL FAIZON: You know, Jeffrey, you’re on our prank show Too Much Tuna where we’re going to deliver too much tuna fish to you...

ALEX BLUMBERG: Nick’s latest project is a lewd, zany cartoon called Big Mouth, which has garnered widespread critical acclaim. And at first glance, it seems like more of the same from Nick — it features a cast of ridiculous characters, from a hormone monster to a clueless gym teacher. But the heart of the show, is the story of two friends navigating puberty. And that part... it’s a departure for Nick Kroll. Because it’s his first TV show that isn’t based on a caricature. It’s based on his own story — his own childhood.

Jonathan and I talked with Nick about the comedic evolution that he’s gone through to get to Big Mouth, how he’s gone from hiding behind these over the top personas, to creating a show that puts him face to face with the deeply personal shame and regret he still carries around from his past.  

And before we get started though, there’s one more thing. I’ve given a lot of language warnings on this show before, but truly none have been more warranted than the language warning I’m about to give right now. There are lots of bad words, and lots of talk about sex in this interview. In fact, the sex talk, it started pretty much the minute Nick Kroll arrived in the studio…

NICK KROLL: Hey! 

ALEX BLUMBERG: Hello! 

NICK KROLL: How’s it goin man?

ALEX BLUMBERG: How are you? Uh, Jonathan's on the line too.

NICK KROLL: Hello.

JONATHAN GOLDSTEIN: Hi. Hi, Nick Kroll. How are you?

NICK KROLL: I'm great, Jonathan. I'm a big fan of yours.

JONATHAN GOLDSTEIN: Oh, come on. That's so nice. I -- I had an anxiety dream last night that I referred to you as a comedic genius. And you got upset. Yeah.

NICK KROLL: [laughs] Oh my god.   I had the -- the worst wet dream I ever had, let's just get into it.

JONATHAN: [chuckle] 

NICK KROLL: Is I couldn't figure out how to get my skis -- like, couldn't get my boots into my skis. And then woke up, and it was -- I was, like, 16, you know? I was -- and had come in my -- in my sleep.

ALEX BLUMBERG: And the dream was like, just putting your feet into your boots?

NICK KROLL: Just, like, trying to get -- like, getting my boots into my skis and, like, couldn't quite get the ski equipment right. And I couldn't figure it out. And [laughter] it is the worst wet dream. But it was perfectly symbolic of where I was feeling about, like, how sex -- like, it was like, I don't know how this works. I don't know how I'm gonna do this. I can't do this well. And -- and then my friend a couple of weeks later told me, he was like, "I had a wet dream last night that I slayed a lion." I was like, "We are having -- we are in different places in our sexual evolution."

JONATHAN GOLDSTEIN: You know, I never -- I've never had a wet dream in my whole life. And I had read as a kid how it was like, boys have a wet dream and girls get their period. So I felt like, because I never had a wet dream, I -- I wasn't becoming a man. So I remember lying to my mother about having a wet dream, apropos of nothing when I was about 13. I told her I had it at my friend Lenny's house. Um, and -- and -- and -- but yeah, I just -- I guess I -- my fear was that I was just -- that I was masturbating too much to actually have, like, anything left over for -- for wet dreams.

NICK KROLL: Well, that is -- that is literally possible. 

JONATHAN GOLDSTEIN: ...yeah. So I wanted my mother to know that -- that …

[laughter]

ALEX BLUMBERG: That that wasn't the case.

NICK KROLL: You were planning out. You were like, "I think my mom knows I'm not having wet dreams because I'm jerking off too much. I'm gonna head that off at the pass and let her know that I had a wet dream, which means she's wrong. I'm not masturbating too much over here."

ALEX BLUMBERG: Well played, 13-year-old Jonathan Goldstein.

NICK KROLL: Yeah, it's a real chess match. 

[laughter]

ALEX BLUMBERG: See? I wasn’t kidding about how dirty it gets, right? Anyway, let’s get back on track here...Nick Kroll grew up the youngest of four siblings, and Nick’s father built his own business: Kroll, Inc., which was a corporate investigations firm. It actually earned Nick’s dad the nickname “Wall Street’s private eye” from the New York Times. And over the years, Kroll Inc., it grew to be big... a large billion dollar business, in fact.

ALEX BLUMBERG: Talking shop about your life story for one second.

NICK KROLL: Yeah.

ALEX BLUMBERG: It presents a little bit of a problem with the beginning, because you come from a wealthy family.

NICK KROLL: Yes.

ALEX BLUMBERG: And so normally you're sort of like already -- like, you're not in -- you're not in a sympathetic place.

NICK KROLL: Correct.

ALEX BLUMBERG: And so we had a long conversation about, like, how do we handle that?

NICK KROLL: Yeah.

ALEX BLUMBERG: Do we glide past it, or do we just, like, dive into it? I want to dive into it.

NICK KROLL: Sure.

ALEX BLUMBERG: How rich was your family?

NICK KROLL: [laughs] My family was rich, but not as rich as the internet claims it is.

JONATHAN GOLDSTEIN: Scrooge McDuck rich or Richie Rich rich?

NICK KROLL: Yeah, um like yes I've broken some vertebrae diving into gold coins. Um...

ALEX BLUMBERG: Did -- did you have a yacht?

NICK KROLL: No.

ALEX BLUMBERG: Did you have a boat?

NICK KROLL: N— uh, we had a boat or two. But a regular size, like -- like 15-foot boat. Never, like, a boat, boat, yacht, boat, nothing like that.

ALEX BLUMBERG: Right. So you were -- you were the kind of rich family that, like, downplays how their -- the size of their boat, rather than plays up the size of their boat.

NICK KROLL: Correct.

ALEX BLUMBERG: Okay. Uh, did you know you were rich?

NICK KROLL: Yes. Uh, yes.

ALEX BLUMBERG: How?

NICK KROLL: Um...

JONATHAN GOLDSTEIN: Robot maid?

NICK KROLL: We have a [laughter]  Uh, we -- let's see. Did I -- did I -- did we know we were wealthy? Uh, well, we had a very nice house. My parents got a -- a really special piece of land. And so that was the most clear and... very clear evidence of our -- of the money. 

ALEX BLUMBERG: Describe the house. What was it like?

NICK KROLL: It's just on the water. So it's just got unbelievable -- you can see New York City, you can see Long Island. It's just a very beautiful picturesque place. And -- and so that's -- that was the thing that I was both, like, proudest of and most insecure about is, like, having friends over and being, like -- and I still do it. I'll be like, "So, you're coming to my parents' house and you should just know that it's -- it's nice." You know what I mean? Like, I …

ALEX BLUMBERG: [laughs] Um, and the money came from your dad’s business, right?

NICK KROLL: Yes. 

ALEX BLUMBERG: What kind of a presence was your -- was your dad? Was -- was he a big presence? Was he -- was he the kind of presence that you felt compelled, like, "Oh, I'm gonna forge my own path here?"

NICK KROLL: Well, you know, I mean, it wasn't like he was famous. Like, you would picture, like, someone being the son of, like, a -- an art -- a writer or a musician or an actor. But he was always known in some capacity. And, like, my friends' parents, like, who were lawyers knew about my dad or something like that, you know? And I think I was very conscious of wanting to go do my own thing and create my own path. Um...yeah.

ALEX BLUMBERG: So, like, what were you like as -- as -- as a teenager?

NICK KROLL: I was, like, a little guy. I was really short throughout middle school and into high school. I started growing by the end of high school. I always thought of myself as funny. I think most people saw me as, like, sort of funny. Like, I don't think -- I don't think, like, my -- the people, my camp or in my elementary school who were watching me at talent shows were like, "This guy's gonna have his own TV show one day."

ALEX BLUMBERG: Right. Nobody was like, "I saw it back then."

NICK KROLL: Yeah.

ALEX BLUMBERG: "He was destined for this."

JONATHAN GOLDSTEIN: What — what did you do as a part of your act at a -- at a junior high talent show?

NICK KROLL: Uh, me and Andrew Goldberg, who I have co-created Big Mouth with, alongside Mark Levin and Jen Flackett, uh, Andrew and I have known each other since first grade and we became best friends in middle school. And, um, he and I would do, like, uh, Wayne's World sketches. We would, like, host the Purim talent show as Wayne and Garth. Uh, and we would sort of do the Madlibs of, like, Wayne and Garth kind of jokes about Aurora, but instead of Aurora it was about Solomon Schechter. Um -- so we were always doing kinds of things like that. Um… yeah, I was also the Pharaoh in the second grade production of Exodus From Egypt. And I think it was just like, I got a lot of parts in -- in elementary school because I just think I talked the loudest.

ALEX BLUMBERG: When did you realize that this was even something that you wanted to do? Like, what -- how did -- how early did you know, like, I want to be on stage? 

NICK KROLL: Well, I mean, I think in reality it's when I got to college...  

ALEX BLUMBERG: College was Georgetown University. Nick was a freshman history major. And as you do as a freshman, he was trying new things. So he signed up for a university open mic, called Funniest Act on Campus, where he caught the attention of an older classmate, a classmate who was also a budding comedian. Mike Birbiglia. 

NICK KROLL: I did, uh, funniest act on campus at Georgetown where I met Mike Birbiglia and I bombed.  

JONATHAN GOLDSTEIN: Do you remember what -- what that looked like?

NICK KROLL: Yeah. I -- I was gonna -- my bit was I was going to get on stage and say, "Boy, I thought I was gonna be so nervous, but I'm actually quite relaxed." And then I was gonna piss my pants. Um, but I didn't believe -- I didn't believe I could actually piss my pants on -- on cue, so my plan was to bring a water balloon and have it in my pocket and pop the water balloon. But then I got so nervous that I got a little drunk, and -- and stoned before the show to sort of ease -- and so then I got to the venue and I didn't bring a water balloon and a pen, and I was rummaging around in the garbage and found like a sandwich bag. And I ...

JONATHAN GOLDSTEIN: Filled it with urine

NICK KROLL: ... filled the sandwich bag with water. With urine. And then took a pen and was trying to stab the sandwich bag on stage to look like I w-- but it just looked like I was masturbating on stage, basically. So -- so I failed at what I was trying to do, and then I decided to explain to the audience what I had been trying to do.  sort of saying like, "Hey guys, here's what -- here's what the plan was."

[laughter]

ALEX BLUMBERG: So...Actually, what I love about that story is you bombed in a bunch of different ways. Like, you bombed and just sort of like -- you just general -- you just generally fucked up and forgot to bring the thing that you were supposed to bring to make the bit work. And then the bit didn't work and it was the sort of that bomb. And then it was like the bomb of, like, trying to explain it 

NICK KROLL: Trying to explain it and sell it all out. Yeah.

ALEX BLUMBERG: So, like, it was a very -- it's a -- it's a -- it's a ...

NICK KROLL: It's a multi-tiered bomb.

ALEX BLUMBERG: It's a multi-tiered bomb.

JONATHAN GOLDSTEIN: It was like, you were gonna inoculate yourself from rejection by almost, like, building that into your routine.

NICK KROLL: Yeah. Yeah. So it was -- I thought I was gonna be nervous, but I'm actually relaxed and piss my pants, which is sort of undermining my own fear and trying to create the joke inside of what my perceived fear of the situation would be. Uh... but Mike saw me bomb and was like, "Boy, he's bombing in an interesting way." 

JONATHAN GOLDSTEIN: That's the highest form of comedy.

NICK KROLL: I think. [laughter] Well, and I think that's what -- and I honestly think that -- my gut is that's what caught Mike's attention. And so I was ju— I got cast in the improv group by Mike Birbiglia, uh, a sketch show freshman year and then -- and then the improv show -- group the next year. And I -- I have a very clear memory of -- going to do a lot -- a table read of a bunch of sketches where I was, like, got to do voices and play -- choose a -- play a character and play a part, you know? Because until that point I had done, like, a few plays in middle school and high school, but it was like Oklahoma.

ALEX BLUMBERG: Right.

NICK KROLL: Um. And so all of a sudden that I was reading, like, modern current sketches and being able to make big character choices. Like, where I was, like, oh, I feel very -- this is very fun and I feel like an ease in this space.

ALEX BLUMBERG: Mhm.

NICK KROLL: And I walked out being like, "Oh, this is what I want to do for the rest of my life." Like, I just had this feeling of like, oh, this is the -- like everything else until then, growing up a kid with -- you know, like, with wealth and privilege, um, you have -- it affords you to not be terribly, like, ambitious, um, in a lot of ways and -- and somewhat passionless, because you just are sort of like everything will be fine, you know? And, um, -- and -- and then I found comedy and it was like, "Oh, I'll do anything and everything I need to do for this. Like, this -- I will do anything.

ALEX BLUMBERG: Coming up, we talk to Nick Kroll about his rise through the ranks of the comedy world. Which for him, involved inventing a bunch of crazy characters, a few of whom Jonathan and I actually get to interview. That’s after the break.

[BREAK]

ALEX BLUMBERG: Welcome back to Without Fail and our conversation with comedian Nick Kroll.

After falling in love with improv in college, Nick moved to New York City with a bunch of his improv friends, like Mike Birbiglia, and another Georgetown alum, John Mulaney. And they all tried to make it in the comedy scene. And like any aspiring stand up and improv comic, Nick still bombed many sets. But on the side, he started doing something that made him think, “maybe I can make this comedy thing work after all” -  he started writing skits with his friends from college.

NICK KROLL: Me and, like, my improv group from college, those -- the -- the guys that I worked with started selling the first versions of, like, web shows to Comedy Central called, like, I Love the '30s. It was a parody of I Love the '80s, and it was people in the '40s talking nostalgically about the '30s of, like, the Hindenburg disaster and the Lindbergh baby kidnapping. And, um…

ALEX BLUMBERG: That’s funny.

NICK KROLL: Me and John Mulaney before that did a newsreel about San.. like a San Simeon newsreel, like cavalcade of personalities.   There's Chuckles Fine. Toast -- toast of Vaudeville. Watch out, ladies. He'll verbally abuse you. That -- there's Joe Joe Bryson, heir to the Bryson clam sauce fortune. 

CAVALCADE OF PERSONALITIES: ...clam sauce fortune. How bout a kiss? Deeelightful! ... Room in the pool for one more ladies? Doesn't matter to Tuddy Maxwell. he wouldn't doff his shirt for all the sand in Cairo...

NICK KROLL: It was a lot of that. It was just this weird, it sort of is what I've -- I guess I've done a lot of, which is take a -- take something that's, you know, some sort of genre thing and -- and -- and speak to the subtext of that thing in a way that, um, it's presented as one thing, and then -- and then you try to present some underlying subtext to what's really going on in those people's lives.

ALEX BLUMBERG: But yes -- but it's also like -- like, you watch it and you're like, this kid's got something.

NICK KROLL: There's something.

ALEX BLUMBERG: There's something weird and funny and, like, unusual here.

NICK KROLL: Yeah. Yeah yeah.

ALEX BLUMBERG: And so Nick plugged away. He showed up at auditions, did standup gigs, went on comedy podcasts... and continued to do his own projects on the side. And always at the heart of what he was doing, were the extreme and extremely funny characters he invented along the way. And those characters, that’s what eventually got him noticed.

In 2011, Nick landed a supporting role on the hit sitcom Parks and Recreation, a show about the Parks and Rec department in a small town in Indiana. Nick played a character called The Douche, a shock jock radio DJ, who relies on crude jokes and crude sound effects on the sound board.

ALEX BLUMBERG: We thought it'd be interesting if we could just interview some of your characters.

NICK KROLL: Sure.

ALEX BLUMBERG: So -- so maybe -- and we sort of came up with some of our favorites. So first we thought we'd start with the Douche.

NICK KROLL: Which Douche? I've played a number of Douches.

ALEX BLUMBERG: The radio DJ from Parks and Rec?

NICK KROLL: Okay. Gotcha.

ALEX BLUMBERG: Yeah. The Douche.

NICK KROLL [as The Douche]: All right. I'm here with Alex Blumberg. And Goldstein's on the phone. Uh-oh! Raaw! Raaw! What do you got boys, what do you got?

JONATHAN GOLDSTEIN: Do you think the podcast Without Fail could benefit by more sound effects, more toilet flushing?

NICK KROLL [as The Douche]: Oh, all right. Well, you know, looking back on a -- I mean, let's just say I don't believe in podcasts, okay? It's terrestrial radio, the future, the current and the past. Don't think I need a podcast, some guy in his garage, typing away at his computer. "Ah. Excuse me, sir. Can you tell me, do you think my podcast would benefit from more sound effects?" Of course it's going to benefit from sound effects. We got uh -- Rob on the ones and twos over there ready to go with a couple

At this point, just to give you a full visual on what’s happening here in the studio, my producer Rob, who was in the studio with us, started frantically googling sound effects websites on his laptop computer. 

ALEX BLUMBERG: Uh, Douche, I gotta ask you. So -- tell me about -- tell me about a -- tell me about a memory from your childhood.

JONATHAN GOLDSTEIN: [laughs]

NICK KROLL [as The Douche]: Okay. First time I saw a big pair of boobs, I uh... 

[AIRHORN SFX]

[DUCK SFX]

NICK KROLL [as The Douche]: Yeah. I was on a -- a duck trip with my dad. We were hunting ducks and then a duck came out with a bikini on. And I said, "Uh-oh! Looks like dinner is served!"

[BOING SFX]

ALEX BLUMBERG: You’re right it is better.

NICK KROLL: It is, it really is.

ALEX BLUMBERG: Uh, Douche, what's your biggest failure?

NICK KROLL [as The Douche]: My biggest failure is doing a podcast.

ALEX BLUMBERG: [laughs] And what's your biggest success?

NICK KROLL [as The Douche]: Uh, doing a podcast. Trying to get a podcast off the ground.

ALEX BLUMBERG and JONATHAN GOLDSTEIN: [laughs]

ALEX BLUMBERG: In 2013, Nick landed his own show, Kroll Show, on Comedy Central. Kroll Show is a sketch comedy show that recreates the experience of channel surfing, skipping around to different parodies of bad cable TV. The premise was a perfect vehicle for Nick to unleash a slew of ridiculous roles, from a pawn shop broker to a pet plastic surgeon to the stars.

My co-host Jonathan Goldstein is from Canada, and so he specifically requested that we interview one character in particular: Mikey from a Kroll Show parody called Wheels Ontario, which was a send up of the classic Canadian teen show Degrassi.

NICK KROLL: It really just became a vehicle for us to do, like, one million Canada jokes. Um...

JONATHAN GOLDSTEIN: But how -- they're so -- they're so specific, and so -- it's just so pitch perfect. 

NICK KROLL: Ooh. Ooh, thank you.

JONATHAN GOLDSTEIN: We do drink bags of milk.

NICK KROLL: Yeah, they do drink -- Canadians drink a bag of milk. Um...  but why don't we talk to Mikey and we'll see what we find.

JONATHAN GOLDSTEIN: So ...

NICK KROLL: Well so, would you like me to be Bryan La Croix, who's the actor who plays Mikey? Yeah, I think I'll be Bryan La Croix.

JONATHAN GOLDSTEIN: Oh, yeah. That's so meta.

NICK KROLL: So you'll be talking to Bryan La Croix.

JONATHAN GOLDSTEIN: Um, Brian, what kind of research did you have to do for your role as Mikey? Did you spend a lot of time in Canada?

NICK KROLL [as Bryan LaCroix]: Em, well, uh, pardon for, um, I'm sorry to correct you, but, um, I was in Canada already doing the research, um, because that's where I'm from. But, um, well I've been leaving -- living in Canada, um, not again -- not against my will, uh, but instead in -- been in the process of being a resident of Canada for many years. And so for that, you know, I'm -- I'm grateful to the Queen.

[laughter]

ALEX BLUMBERG: Uh, Bryan.

NICK KROLL [as Bryan LaCroix]: Mm-hmm?

ALEX BLUMBERG: What's your -- what's your biggest failure?

NICK KROLL [as Bryan LaCroix]: To be honest, my biggest failure is as a friend. Um, [laughter] I don't -- I think I've -- I remember a friend of mine, uh, asked me to come over one night and I couldn't do it. And I -- I felt like I failed him as a friend. And, you know, I've sent him a number of sorrys and a number of pardons. But yeah, I don't think he ever quite forgave me.

JONATHAN GOLDSTEIN: Alex, you must have some follow-up questions.

[laughter] 

ALEX BLUMBERG: And then, in 2017, Nick launched Big Mouth, an animated series, which would go on to become his most critically acclaimed show, and in which his ability to create iconic and memorable characters was on full display. Nick voices a character based on his own adolescent self, but he also voices more than 20 other characters, including the hormone monster and a character named Coach Steve. 

NICK KROLL: Coach Steve is the -- gym teacher on Big Mouth, and um, I think possibly one of the dumbest characters to ever exist.  

JONATHAN GOLDSTEIN: So tell -- tell us -- tell us a little bit about your childhood.

NICK KROLL [as COACH STEVE]: Oh, my childhood was great. Oh my God, I had the best childhood, you know? My mom -- you know, my dad was gone a lot and my mom had this guy named Gary, and he would come over and do push ups on my mom, when my dad was gone.  And, uh, what else about me, you know?

ALEX BLUMBERG: Did you have friends?

NICK KROLL [as COACH STEVE]: Oh, sure. Yeah, I had a bucket in my room that I would -- you know, that I could do whatever I wanted with. And he was cool.

ALEX BLUMBERG: Wait. A bucket?

NICK KROLL [as COACH STEVE]: A bucket, you know? Yeah. I could put all my -- my stuff in it and my feelings and the bucket would take it. And we were so -- we were great friends.

ALEX BLUMBERG: I'm sorry, Coach Steve I was asking -- I asked you about -- about -- about your friends.

NICK KROLL [as COACH STEVE]: About my friends?

ALEX BLUMBERG: Yeah.

NICK KROLL [as COACH STEVE]: Yeah, there was my friend the bucket. And then who else? And then I had a broom. And I could put the broom -- if I turned the broom upside down, it was like a lady from a band and she would play music for me. And we were close. So it was cool. It's pretty cool childhood overall. It was pretty fun.

ALEX BLUMBERG: Um, what -- what's -- what would you call your biggest -- biggest failure?

NICK KROLL [as COACH STEVE]: My biggest failure? Man, you know, my biggest failure -- you know, I would say that my greatest weakness is that I have no strengths,  

[laughter]

JONATHAN GOLDSTEIN: That was wonderful.

ALEX BLUMBERG: How do you do that?

NICK KROLL: What?

ALEX BLUMBERG: What you just did?

NICK KROLL: What I did? Oh well, he's the freshest. Of all three of those characters, I feel like, to be honest with you, I feel like I gave you guys B minuses, two B minuses and a B, to be frank, in my character improvisational abilities inside of that. Because I don't -- I felt like I wasn't fully dropped in. There are times where I can drop in where I am like ...

JONATHAN GOLDSTEIN: You feel like you're channeling it ...

NICK KROLL: Yeah. Do you know what I'm saying? It's like that -- it's the closest, like, I can get to a flow state where I'm like, oh, I am -- I have access to this whole person's life right now.

ALEX BLUMBERG: And what does it feel like to drop in? What does that mean?

NICK KROLL: It just means there's no filter. There's no moment where I have to come up with something. Like -- like we were -- we were doing a panel up in -- in Montreal actually, and I was doing Coach Steve for a second. And, like, I had a moment where I'd go as Coach Steve, I was like, "You know, but at the end of the day, it's night." And like -- like it -- it -- you know, it's like that's the some version of the flow state of like, "Oh, I think I can -- I can start a sentence and I think by the end of it I will have come up with something, uh, funny."

ALEX BLUMBERG: And -- and you didn't -- you started that sentence not knowing how it was going to end.

NICK KROLL: Correct. Correct. 

ALEX BLUMBERG: In other words, it's as  -- in that it's almost as funny to you as it is to everybody else because it's almost like you're hearing it in real time like we are.

[CROSSTALK]

NICK KROLL: Yes, it is. It's like -- I'm like, if I can start a sentence with -- with something that feels rote, like, you know, "At the end of the day," I'm doing the math while I'm saying "At the end of the day" that by the time I finish that sentence, I will find what the -- the proper, like, mathematical solve is for it. And I can do it, like, you know, in real time, at times. That's what feels like when you're in the flow. When I -- when I feel like I'm sort of flowing in -- in -- inside of the characters.

ALEX BLUMBERG: So what -- what was it about, like, doing the characters all the -- all those years that was attractive to you? 

NICK KROLL: Um, well, there's a safety in hiding behind the character. There's a safety in, like, um, not exposing myself. There's a safety in -- um, in being able to boil someone else down to an archetype or -- or whatever. To build someone else's world is -- is -- feels safer and easier than trying to disseminate what, like, my world experience is, or what my point of view on an issue is. Like, if I see a car crash, I can tell you what Coach Steve is gonna think or what the hormone monster's gonna think. It's much more complicated for me to tell you what I'm -- what I think about seeing that car crash. 

ALEX BLUMBERG: Why?

NICK KROLL: Um, because I think our points of view, or at least my point of view is m-- is -- is -- it's just more complicated because I see a car crash. I know that’s a weird example, but let's just use it because I'm trying it, I'm immediately like, um, "Oh, man. Like, who is in that car? What -- do they have a family? Do they have insurance? Like, what is going on with our healthcare system? Um. What's gonna happen to traffic right now? Am I gonna be able to get into the city in time for my appointment tonight? What if my parents were in a car crash? What if my sister was in a car crash? Um. Like, I don't -- oh, that car has a ton of scrapes on it. That person's a bad driver." Like, dah, dah -- like, I'm -- I'm -- I'm -- I'm having in my mind 40 thoughts run through my head. If the hormone monster sees a car crash, he's -- he -- he's like -- [as the Hormone Monster:] "Oh, have you seen that scene in that movie where the guy fucks the car crash-wounded person?"

JONATHAN GOLDSTEIN: It's -- it's simpler. It's -- it's your consciousness is constantly fragmented.

NICK KROLL: Exactly.

JONATHAN GOLDSTEIN: And then you -- it must -- there must be just something kind of not comforting, but -- but just kind of simple.

NICK KROLL: It's a simpler -- it's simpler to -- to present someone else's point of view.

ALEX BLUMBERG: Well, it's not that you're presenting someone -- it's not just presenting someone else's point of view. It's like, someone -- it's like a very specific -- it's a -- it's a caricature's point of view. It's like a person -- it's a person who takes, like, just one aspect of the multitude things of things that you're feeling and that's all they feel.

NICK KROLL: Yes. It's simpler. Even though then the more that I get inside of those characters, the more that you can start to build these backstories and you realize how complicated and nuanced their lives are, and all of that stuff can play into that. But even then you are cherry-picking a very clear, definable example of what their reaction is.

ALEX BLUMBERG: Coming up, Nick learns to start sharing more of his own backstory, thanks to a therapy to writers room feedback loop. We’ll explain what that is, after the break.

[BREAK]

ALEX BLUMBERG: Welcome back to Without Fail and our conversation with Nick Kroll.

For many years, Nick had built his career playing characters. So when he created the cartoon show Big Mouth with his childhood friend Andrew Goldberg, the animation gave him license to fill the cast with even more outlandish characters - in addition to Coach Steve, there’s the hormone monster, who you briefly met before the break…

HORMONE MONSTER: You ever actually fuck a tomato? It’s like fucking a sneeze. [Wait, you find a sneeze sexual?] Ooooh, I find everything sexual...

ALEX BLUMBERG: … the hormone monstress…

HORMONE MONSTRESS: [Why do you smell so good?] Because I don’t use deodorant and I only take bubble baths...

ALEX BLUMBERG: … and the ghost of Duke Ellington, who lives in cartoon Nick’s attic... 

GHOST OF DUKE: Jazz is like life! It goes on for longer than you think, and as soon as you’re like, “oh, I get it” — it ends! Hahaha!

ALEX BLUMBERG: These characters play supporting roles to a group of adolescent teenagers as they navigate the onset of puberty. Big Mouth focuses in particular on the friendship of Nick and Andrew. And it’s based in part on the real friendship that Andrew and Nick had as kids. Andrew hit puberty earlier than Nick did, which was hard on their friendship, hard on Nick.

And the process of using his own life as comedic material, instead of pee bags, air horns, and Canadian references? It’s been new for real-life Nick. 

NICK KROLL: You know we started doing Big Mouth, which was really my story about what it was like for me to grow up and be a 13-year-old boy who hadn't hit puberty and who was dealing with what the ramifications of that were for him. And really what the ramifications are for me as a man, now a 41-year-old man who is still dealing with some of the -- many of the elements of what -- who I was as a 13-year-old boy. Like, I think puberty is such a formative time for people that it -- it has effects on us in ways that we can't even quite -- quite fathom on a day-to-day basis. But — 

ALEX BLUMBERG: Oh yeah.

NICK KROLL: So -- so -- and so I would go to therapy and then I would go to my room...

ALEX BLUMBERG: Go to your room. Your writer's room.

NICK KROLL: Sorry, my writer's room I'd go to my writer's room and, and then I would go to therapy, and I would realize that I was -- they were informing one another  

ALEX BLUMBERG: What -- you said that -- that the experiences from, like, puberty really continued to affect you even well into adulthood, which I think is -- I think it's completely true. Um. I guess in this process of, like, making the show and therapy, the therapy-show feedback, what have you learned from -- about yourself?

NICK KROLL: I think, like -- I think it's partly like being a little guy, um, like being, like, 13 and -- and not having hit puberty and looking around, like being at camp and being in the showers and, like, looking to see who had, like, an adult penis or look who had, like, pubes or look who's, like, his nipples were swollen or eyebrows had grown in or, you know, the things that, like, I had known were secondary sex characteristics. And just like a lot of compare and despair. A -- a lot of sort of like trying to gauge where other people were and then gauging myself based on that and seeing if that -- whether I stacked up or not. Um you know, people ask me all the time like, what advice would you give your 13-year-old self? And I -- and it's like -- I would, like, tell him, like, you're cute. Like, you're -- you know, like, you're a good kid, you know? Like -- and I knew I was a good kid. Like I mean, I knew I was -- it wasn't like I had low self-esteem, but I did. And I do, you know? Like, we all kind of like -- nobody hates -- nobody hates you as much as you do. And like, I don't know, at least that's how I feel. Like, in doing this show of -- of exploring who I was and who I am, it's like, to just try to be a little kinder to myself, which is such a long -- it's like a lifelong -- and then look, there are certain people who are, like, way too kind to themselves, but I think there's a broad swath of us who are not so kind to ourselves.

ALEX BLUMBERG: What were you not being kind to yourself about?

NICK KROLL: Um, about, like, what I looked like and what I -- and -- and how, like -- like the -- like -- like, looking around -- and it's -- it's -- none of it makes any sense. Like, I am a incredibly successful comedian and writer and actor, and I know that I have succeeded beyond what my highest expectations of what I would have hoped I could have succeeded at. I have done that. And I've surpassed that. And yet I can watch Jason Mantzoukas improvise or watch John Mulaney do stand up or see Jenny Slate do a character and be like, "I'm fucking garbage." You know? Like, I'm terrible. Look at them. Like, that is success. That is talent. The only reason I get to do this is because I put the show together myself. That's how I get to do these things, you know? Like, I'm not as talented. Which is just an extension of me being like, Andrew has pubic hair and a big dick and muscles. And I'm, like, this little boy who's sitting here, you know, with, you know -- who's got like, a little -- little bald little cashew. It's all extensions of the same stuff, I think. 

ALEX BLUMBERG: Hm. Was there -- was there anything in the process of -- of doing Big Mouth where you admitted something about your past or your present that you had never told anybody?

NICK KROLL: Um. Yeah, you know, like, there's an episode in season two where Nick -- a girl -- it's an early episode, this girl Gina, voiced by Gina Rodriguez, is a girl who's been at the school for a number of years and she grows boobs all of a sudden. And it was like a kind of a typical middle school story where it's like all of a sudden some girl grows boobs and, like, everyone's, like, eyes are on her. Like, "Whoa, who is she? Who's the new girl?" It's like, she's not new. She just grew breasts. 

GINA: Please do not bring up science, that class is killing me! 

NICK: Maybe I can help! I don’t want to brag, but I am getting a low B , so…

GINA: Ugh, I’m like a full C…

NICK: Mhm. [gulp]

JAY: Nick is so lucky!

ANDREW: I can’t believe he can just walk up to those boobs and then.. say...things…

NICK: Just spitballing but maybe we should study together...

NICK KROLL: And I -- I remember, like, making out with or fooling around with some girl who was a year ahead of me who had big boobs, you know, when I was that age, I was so little and I wanted to, like, date the girl with the biggest boobs to show everyone that I could get the girl with the biggest boobs. To show that I was, even though I was a little guy, I was like a  -- I was a man, you know? Um...and then I, like, bragged about it and it was fine. Like, she didn't -- she wasn't, like, lambasted for it, but like -- but that feeling of being, like, honest about being, like, I did that so that I could tell everyone that I did that, um, is something that, like, uh, I probably had not ever kind of been very open about, or being like ...

ALEX BLUMBERG: You'd never fully come clean.

NICK KROLL: Yeah, I think so. Yeah. 

JONATHAN GOLDSTEIN: It's a surprisingly difficult thing to do. I find like with a lot of the stories that I do where let's say, like, you know, I -- I go with someone who's been bullied by a group of kids and, you know, it's, like, 30 years later and we go to get the other kids to talk about what went down at that time. And there's an incredible allegiance that people feel to their past selves, or it -- or it doesn't even feel like the past. It feels incredibly close. Like, we'll -- you know, talk to one of these bullies and -- or -- and they'll just -- they won't want to go on the record, you know? Like, it's -- it's kind of a phenomenon.

NICK KROLL: Even though it's 30 years ago.

JONATHAN GOLDSTEIN: Even though it's, like, 30 years ago. Yeah. They just feel a lot of embarrassment about it and shame, I guess. And, um -- and yeah.

NICK KROLL: Yeah. It's a lot -- that makes perfect sense. And I think it's like, you know, look, I've -- I've been rewarded for being vulnerable about who I was as a 13 year old. Both having a show and financially. So I can under -- it's easy for me to do that because I have been rewarded for it. Like, for the bullies you're talking about, like, I could see them being like, "What's in this for me?"

ALEX BLUMBERG: What's the upside?

JONATHAN GOLDSTEIN: Yeah, there's a lot of that. Yeah, that's true.

NICK KROLL: And I think -- but what I think they don't realize is that there's catharsis in it. There's catharsis in coming clean about who you were. Um, you know, season two of Big Mouth focused a lot on this character The Shame Wizard, that was really more Andrew Goldberg who -- who really came up with. And he said, "I want to do a shame monster." And I said, "Maybe it's not a shame monster. It's a shame wizard." 'Cause, like, there's something haunting and slightly magical and -- and evocative about a wizard more than a monster. A monster has no -- has no, um, couth.

JONATHAN GOLDSTEIN: A monster's also, yeah, it's, like, endearing. It's like, you know, like Oscar or, like, Grover from Sesame Street is a monster too. But the wizard is like more -- is like more powerful somehow.

NICK KROLL: Exactly.

JONATHAN GOLDSTEIN: And darker.

NICK KROLL: And I think that's what shame was and is for so much of us, that it's a really seductive kind of emotional state. Um. And -- and I think so much of shame is built from that -- starts at that age as you're -- as you're getting sexual desires and what is turning you on or how it's turning you on or who's turning you on or -- and how your parents react to that, how culture reacts to that, how your friends react to that. Um...

ALEX BLUMBERG: And there's all these things that you're not allowed to talk about. Like -- like we opened this up, like, talking about wet dreams and I'm like, "Do we have to cut that from the podcast?" You know what I mean? And it's like, maybe ...

NICK KROLL: Maybe you do, maybe you don't. It's this ...

ALEX BLUMBERG: Listeners, you will know.

NICK KROLL: You'll find out. But if it got cut folks, we started talking about wet dreams. But it's -- and for me it's like, you know that -- that's clearly a tool for me that I have, from doing the show, where I'm like, "All right, well I'm gonna talk to them immediately about my weird wet dreams because it's -- it tells you like, I'm here to be open with you, I'm here to, like, share with you." And if I do that with you, then there's some sort of contract that I can tell whether you're gonna do that back with me, and we can have a real conversation.

JONATHAN GOLDSTEIN: That's why I talked about masturbating, I don't really masturbate. It was an interview technique.

ALEX BLUMBERG: It was just to break the shame spell.

NICK KROLL: Thanks, Jonathan.

ALEX BLUMBERG: With ...

NICK KROLL: Yeah, it's -- and it's -- but it's -- those are real things. And like, I've found it to be challenging at times and scary to be -- continue to be revelatory about myself. But I have -- I have reaped the rewards of it in that I think people have been drawn to the show in a way because it speaks to my experience, but it really speaks to everyone's experience. The universality of the feelings of -- of -- of alienation, of fear, of lust, of -- shame, of anxiety, of all those things that you feel so deeply in adolescence, and then you carry with you for the rest of your life.   And hopefully in sharing that stuff, there's -- there's something universal about it of what it's like to, you know, be broken up with or whatever those things are that we're all going through.

ALEX BLUMBERG: The third season of Big Mouth is out now on Netflix. Nick is also touring with a new standup routine, called Middle-Aged Boy. He says he’s trying out some new material... that’s a bit more revelatory and vulnerable.

Without Fail is hosted by me, Alex Blumberg... 

JONATHAN GOLDSTEIN: and me, Jonathan Goldstein! It is produced by Molly Messick, Rob Szypko and Heba Elorbany. It is edited by Alex and Devon Taylor.   

Mixing by Kegan Zema and music by Bobby Lord.

If you like Without Fail, without me, because I’m never gonna be on it again, please follow the show! If you want to check out Heavyweight, you can also follow us too. You can get every episode for free through Spotify, or wherever you get your podcasts. Thanks for listening.