Exclusive Interview: Pop Culturalist Chats with Pete Lee

From overcoming stage fright to becoming the first comedian to get a standing ovation on The Tonight Show Starring Jimmy Fallon, Pete Lee tells us all about his incredible journey in comedy and his new Showtime special, Tall, Dark, and Pleasant.

PC: How did you discover your passion for comedy?
Pete: I have a grandmother who is really funny. She was a lounge singer in Vegas. She also sang in Los Angeles. Back in those days, if you were an opening act, you had to tell a couple of jokes in between. So my grandmother did stand-up comedy during her set.

I remember one time while we were on vacation, my grandmother asked me what I wanted to be when I grew up. I was like, “I want to be a stand-up comedian.” She was like, “Okay, so write a joke.” I was like, “Well, I’ll wing it. That’s what everybody says when it comes to stand-up comedy.” She was like, “No, you have to have material. It’s hard work.” She taught me how to write a joke and then wouldn’t let me eat dinner that night until I wrote a joke that was an actual joke.

I wrote a joke about a moped. I was too young to even ride a moped, but I thought mopeds were really funny. There was one outside of where we were at. So my joke was, “Do you ever drive with no pants on? I do. I love to drive with no pants on, but I can never tell if people are staring at me because they know or if it’s because I’m driving a moped.” I made my grandma laugh really hard and I got to eat dinner. [laughs] I remember afterwards, my dad was like, “I’m so happy that you wrote that joke because it was bordering on child abuse that we weren’t feeding you.” [laughs]

That was the start of it. I’ve had anxiety my whole life, so I didn’t ever want to get on stage. In college, I would be really funny in the dorm cafeteria. I had this roommate named Tim. He was an author. He had written several novels. He would do guest columns in Sports Illustrated, Reader’s Digest, and all these different publications. He was really focused on writing. He kept telling me, “You’re really funny. You need to be a stand-up comedian.”

We would go down to the dorm cafeteria. I always thought he was doodling in a notebook. It turns out he was writing down all the funny things I said at dinner, like stories that I had about my day or reactions that I had to other people’s stuff. At the end of the year, he gave me that notebook. He was like, “Dude, this is the foundation for your stand-up.” He was like, “I took the time to write it down. You take the time to really look at it.” I looked at it and I was like, “Man, I have to do stand-up. This is pretty funny. But now I need to get up the guts to get on stage.”

I continued to tell jokes during college. I would tell them at parties, almost like Marvelous Mrs. Maisel, where I’d be sitting on the edge of the couch. My friends would dare me to get out my notebook and tell jokes. I’d make the whole room laugh. But I was terrified to get on stage.

Finally, my friends took me down to Acme Comedy Club in Minneapolis under the guise that I was going to go watch the show with them. When the sign-up sheet came around, they put my name on it. When the list of performers came out, I was on it. I had an hour to prepare and go through my notebook and figure out what I wanted to do for my three minutes.

I remember I got up there and I was killing it—I was absolutely crushing it—but I was terrified to be on stage. My ability to overcome my social anxiety didn’t match my stand-up abilities. I remember in the middle of it, I got the biggest laugh of the whole set when I said, “I’m scared. Can I go now?” The crowd laughed so hard. The guy with the God mic in the back of the room was like, “No, you have a minute and a half left.” I told another minute and half’s worth of jokes and got off the stage.

There was a comedian named Nick Swardson. He’s a popular comedian in LA and whatnot. He saw me. It was his last night in Minnesota. He came up to me and said, “Dude, you’re really good. I want you to open for me in April.” I was like, “I don’t even know what that means.” So I knew that I had to keep doing stand-up comedy because I had to open for Nick in April. I kept going at it and then I got to open for him. That was my first paid gig.

It was a long time coming, but I also feel like I got really fortunate. I caught lightning in a bottle.

PC: You’ve had a lot of success throughout the years. When you look back, is there a particular moment that stands out to you?
Pete: In 2017, I got to make my debut on The Tonight Show Starring Jimmy Fallon. The way that came about was so unique. I was at a stalled point in my career. A friend of mine told me to read the book, The Secret. I didn’t read it. I watched it on YouTube. The Secret is all about manifesting your destiny by saying things out loud and making them come true. In the middle of the documentary, it said, “Now’s the time when you press pause and you wish for something unreasonable.” I was like, “All right. I want Jimmy Fallon to come see me at a comedy club.” He had done that for a friend of mine, Nate Bargatze.

I was like, “I want Jimmy Fallon to come see me at a comedy club. I want him to instantly love me, and then I want to go on The Tonight Show. If I’m asking for something unreasonable, I guess I’m also going to say I want to get a standing ovation.” Two days later, I got an email saying, “You have an audition on Sunday for The Tonight Show.” I was like, “Wow, that’s crazy. It worked.”

I’m standing at the bar. I’m drinking whiskey because I’m nervous. The manager of the club walks by and then the owner of the club. Both people stared at me because I didn’t know who was behind them. It was Jimmy Fallon. He was like, “Oh my God, Pete! Dave told me to come see you. It’s really nice to meet you. I can’t wait to see your comedy. He said it’s right up my alley.” The only thing I said to him was, “The Secret is real.” [laughs]

I go downstairs and I’m doing my set. I have this joke where I say, “I never want to offend anybody.” My comedy is the opposite of most comedians in that I don’t want to make anybody feel bad. I don’t want to be edgy. I want everyone to feel good. So I go, “I never want to make anybody feel bad. The other day this guy sneezed. I didn’t want to say ‘Bless you,’ so instead, I said, ‘Happy Holidays.’” Jimmy Fallon stands up, claps his hands, and goes, “Yes! I love this guy!” I wanted to say, “Thank you, Jimmy. I love The Tonight Show,” but instead I go, “Thank you, sir! I love your impulse control.” It got a big laugh. He was like, “Thanks. I don’t have any.” Then he invited me on the show that night!

It was Cinco de Mayo. I got there and I did my set. It was pure magic. I got a standing ovation. It was such a lightning in a bottle moment. I remember I’m standing on stage and Jimmy’s going, “You’re getting a standing ovation right now on The Tonight Show. This is huge!” I thought there was a sign above me that said, “Audience, please stand up now.” You know? [laughs]

I’ve done The Tonight Show five times since then. I’ve had really great sets, but didn’t always get a standing ovation. It was a truly special experience. It changed my life because that video went viral on the internet. I started to get bookings, and then that led to me doing a second appearance, which also went viral.

I had just gotten dumped by my agent in New York. I was with this small agency. Then The Tonight Show happened a week later. A week after that, I was meeting with CAA in LA and they were signing me. It was a truly life-changing moment.

PC: You’ve got a new special out now on Showtime. Tell us about Tall, Dark, and Pleasant and what audiences can expect!
Pete: Yeah! It’s my new special on Showtime. My whole point of view is how much it sucks to walk around the Earth and be a nice person. [laughs] I never really say that on stage, but that’s the crux of it all.

My humor is pretty universal. Everyone can watch this special. Everybody struggles with the same things. There’s a lot of pain in that, and I try to bring people joy. I’m a people pleaser. I’m from the Midwest. I feel like, especially after the pandemic and everything that we’ve gone through, my special is an hour where you can take a break and set everything down and laugh your ass off. You can forget about everything for a little while.

I really want it to be escapist television. I put all my best material from the past twenty-three years into this because I have one rule: don’t save anything. Don’t save anything for later. Blow it all out because you might not get another chance. I really blew it out, and I want this to be something where people watch it and feel good from it after experiencing a year where we didn’t feel very good at all.

PC: What is your creative process like when you’re putting together a special? Has that changed throughout the years?
Pete: Putting together a special is like putting together a late-night set. You have your base material and then you have to figure out the connective tissue because you have funny bits and some go together and some don’t. The hard part is connecting it all. Sometimes the funniest things that you say come from that connective tissue. Like there’s this joke that I have that’s become a meme now. I literally riffed it the night before my first Tonight Show appearance. I riffed it on stage because I was trying to find a connector between two things. It’s just a two-liner where I go, “I hate conflict. I hate it. Unless you guys like it, and then I love it.”

When you’re putting together a special, it’s similar to a late-night set, but it’s an hour long instead of five to six minutes. Some comics that I’ve seen do specials, they just try to go up there and see if something happens in the moment where it seems cohesive. I’ve seen that fall flat and I’ve seen that succeed, but I don’t like to take that chance.

For this special, I spent months getting on stage and working out this material and really tightening it up. That doesn’t mean that the whole thing was scripted. I’m always open to going off the cuff or improvising. There were things in the special where I literally thought of it that night on stage because the crowd was magical.

It was really cool. The material that I wrote for the special I started writing twenty-five years ago. There were little notes from back when I was in that two-year period where I was scared to get on the stage. You have twenty-five years’ worth of material in this special, and I’m still working on it while I’m on stage. I’m still coming up with new things.

It’s an interesting process. The work isn’t done until it’s done. When you write an article, it used to be that you would write an article and you’d print it. It was locked. It was done. Now that things are digital, you can go in and amend something. But with this, we did all the editing for it. I was involved in the editing process. Once that’s done, they call it picture-locked. It’s like, “This is my homework. I’m handing it in.”

A lot of my friends are very hard on themselves about their specials. They go, “Oh, my special’s coming out and I don’t really like it,” or “I didn’t like something that happened in the editing,” or “I didn’t like the crowd that night and I feel like it shows.” I feel like I worked really hard on this and the crowd that night was amazing. I had a blast on stage, and that came through in it. I was involved in the whole editing process, and when I look at the final product, I have to say I feel so proud of it. So I’m glad that I didn’t hold anything back or save anything for the next special.

To keep up with Pete, follow him on Twitter and Instagram. Catch Tall, Dark, and Pleasant on Showtime today.