Judd: That’s why I stopped doing stand-up for so long. The same psychology: There’s no reason why anyone would ever want to listen to me. Then I read somewhere that the best gift you can give other people is your story, and it just hit me, like, Really? That’s the whole thing? And then I thought about who I liked, and how they were going about it.
Key: Like with Bill Cosby: all he’s done his whole career is tell his story.
Judd: Or part of it!
Peele: Yeah. But I want to get back to being a chameleon: So much effort has been put into becoming other characters and becoming other identities. I remember the first time I faced this was when I went to iO [formerly ImprovOlympic] in Chicago, maybe fifteen years ago. And improv is a totally different form. The playing around was fun, but the monologues were so hard. Right before we started doing the show, I tried stand-up for the second time in my life and I realized that if I didn’t have a sense of who I am, the show would just be these empty characters—and they wouldn’t connect. So I started piecing together a few short bits that exemplified my place in the world, and that was the missing element that is so important and has really helped us in the show. Especially with the car segments. Four years ago, I don’t know if I would have had the ability to say, “All right, just be yourself with Keegan. Just do what we would do in a car.” And that was such an important lesson.
Judd: I think those segments are more revealing than being in front of a crowd.
Key: For me, the big challenge is that I am still in this place where I care about what other people will think. It reminds me of something you said, Judd, that has been working inside of me: I have life rights. So I’m going to write this character and Albert Brooks is going to play the character and I know it’s my dad. And I don’t care because I have life rights. It’s my story. I’m trying to find a way to install that idea into me.
Judd: That you’re allowed to do that.
Key: Right.
Judd: These things also get complicated when you feel abandoned. You worry that if you talk about your life and your family that people will abandon you again.
Key: And how can you navigate that? Yeah, it’s tricky. This is why I didn’t go into stand-up. When my dad was still alive, I said, “I want to do stand-up like Eddie Murphy. Maybe I could do that.” And he was like, “Well all right, but don’t tell any jokes about me.” He just straight-out said to my face, “Don’t tell any jokes about me.” Nigga, you are the jokes. You’re like seventy percent of the jokes!
Judd: I sent my dad the script for This Is 40 and said, “It’s fabricated, but it comes out of certain aspects of our relationship.” And he said, “Well, as long as he’s likable. Just get someone funny to play me.” I’m like, “Albert Brooks is doing it.” And he’s like, “All right.”
Key: He signed off on it? That’s great.
Judd: What made you think you actually could do comedy as a career? Jordan, you were in New York and went to a nice high school, right?
Peele: Yes, I was at the Calhoun School but I was the artist kid, very quiet. My mother would have never guessed that I would have gotten into this. But when I was ten years old, I saw this play at this place called Tada, a children’s theater, and it was amazing. I thought: I have that, I can do that. So I went and auditioned. I sold the fuck out of this audition. They asked me to sing “Happy Birthday” and I sold it. I got down on my knees and—
Judd: You went James Brown on them?
Peele: Total James Brown.
Judd: How old were you?
Peele: Ten. And I got the coolest part in the play and very quickly I realized that I loved doing it. It was like, Okay, I actually have a knack for this, and they saw something in me that was probably just that love of what I was doing coming through. From that point on, I started auditioning for commercials. Didn’t get any parts, which disheartened me and left me with this feeling of Maybe I don’t really have a place in this. I don’t know what I’m selling. It was intense.
Judd: I wanted to do commercials as a kid, too. I got head shots made like in seventh grade but I got the chicken pox and had these terrible scars, and they refused to heal. They were red and full of pus and then I actually shoved poison ivy up my nose to make my friends laugh—
Peele: Oh, fuck.
Judd: So I got poison ivy all over my face, plus the chicken pox, and I didn’t know what to do, so I put poison ivy medicine on the chicken pox, which made them blow up like ten times the size—which caused these horrible scars and the pus. And so my dream of acting was over.
Peele: How old were you?
Judd: Between seventh and eighth grade. But that’s what I wanted to do, was go out for those Jack in the Box commercials.
Peele: That’s a really fucked-up time to be selling yourself, too.
Key: The most fragile time.
Peele: I remember one audition I went on, for some kind of fast-food spot. I got in and homeboy was like, “All right, dance.” Oh my God, I busted out and danced. I danced for about sixty seconds. He was like, “All right, great, great, great…” And then you don’t get the gig. I just went there and danced on cue.
Judd: Oh my God. I just found this old tape—a recycled three-quarter-inch tape that I was putting my stand-up act on a long time ago to use for getting gigs and whatever. And apparently it had also been used as the audition tape for a dance party show on MTV. I started watching it and my roommate, Adam Sandler, shows up on the screen. It’s his audition! They put music on and he’s dancing, walking up to other dancers, asking them questions, dancing the whole time. It was as humiliating an audition as you could ever imagine. “Hey, buddy, where ya from? You like this song? Yeah, I like Tiffany, too.”
Key: “I like Tiffany, too.” Oh that’s awful.
Judd: But how did that—all the early acting stuff and the commercials—lead to becoming aware of improv and Second City?
Peele: For me, that didn’t happen until college. I went to high school and did a couple of plays, got into college, Sarah Lawrence. I was interested in theater. My thing was doing puppetry.
Judd: Getting laid a lot?
Peele: Did not get laid as much as I would have liked to. But the need to be liked by girls was a huge motivator. Just to try and make something beautiful because I never had any wild man machismo. I never had any of that shit that the girls like, that X factor. And so.
Key: Well, you have, like, the Beautiful Mind X factor.
Peele: Yeah, but when you’re young, that’s worth nothing.
Key: When I was fourteen or fifteen, I used to listen to that 1977 compilation SNL cassette and warped it in my dad’s van. Warped it because I just listened to it all the time, and that’s how I first found out about sketch comedy. Then I saw an NBC special about, like, the biggest star in the world right now is John Belushi, and they showed clips from Neighbors and an old Samurai sketch. And I just started reading about everything John Belushi did, and about how he started at Second City, but it felt like there was no way to get there, you know? There was no conduit. I didn’t know about improv until a guy I went to college with at the University of Detroit said, “I’m going to start an improv group called New and Improved,” and I said, “I’ve got to jump in here and audition for this.”