Step Inside the Intriguing Mind of Comedian Pete Holmes

The “Crashing” creator Pete Holmes discusses weed hangovers, “coming out” as a comedian and being scouted by the manager of a haunted house.
Step Inside the Mind of Comedian Pete Holmes
Courtesy of Imagine Artist Management

In the current world climate, a seemingly catch-all greeting is, “crazy times,” and for Pete Holmes, he’s mindful of the difference between “crazy times” for comedians adjusting to life without the stage and for people who now have to homeschool their children.

When we connected with Pete Holmes by phone, we recall running into each other—pre-pandemic—at a Los Angeles Mexican restaurant, a seemingly different era where Pete Holmes found himself chasing his baby daughter around the dining room.

For Pete Holmes, becoming a father has changed his restaurant experience—and his life—or the better, and while both may have been turned upside down this past year, he’s kept busy promoting his book, Comedy Sex God, running his popular podcast, “You Made It Weird with Pete Holmes,” and working on COVID-safe productions. Over the course of our conversation, we explore the motivation of Pete Holmes that encouraged him to pursue stand-up comedy, his experience attending your typical Quaker grade school and losing his weed virginity at the tender age of 28.

Pete Holmes—Funny Man and Family Man

You mention your life changing after having your daughter. How did having a child impact you creatively?

Pete Holmes: The style I used to write was just very different. There was so much “me” time. I’m a big believer that whatever you do—if you’re a writer—whatever you do is writing. Going to the movies in the middle of the day is writing. Taking a nap is writing. Taking a day off is writing. Going for a walk is writing. So all of that “down time” was really good to my process.

An idea would usually get me out of bed, whether it was a joke, a tv or movie idea—whatever it was—it would literally wake me up because I was so rested. I’d be getting up at 5 a.m. to write—getting up when it was totally dark—and would sort of finish my day as a writer before anything else started. It was like robbing a bank or something. Before noon, I’d gotten all of the day’s productivity out of the way and then could just do whatever, which was great. Now, my daughter gets up around 5 a.m., so what happens is, you adapt.

My wife Val and I think back to our life before the baby and—I’m not just saying this because it’s an interview—our life is richer, more meaningful and more fun than before. Val’s helping me recognize that my process for being creative is to disrupt it. So if you’re sleeping a lot, sleep a little. If you’re not exercising, start exercising.

If you’re seeing friends, try to be reclusive. If you’re being reclusive, go out and see friends. Whatever it is—whenever you start to plateau—shake it up. In my experience, our system of creativity benefits from disruption. Now, I get up and I’m with my baby and that really throws me off my axis. My life is so weird that I don’t have to make it weird, and in that way, it’s really good for my creativity.

When I’m rocking my baby, I’m not deliberately thinking of ideas, but they do show up. The number of times I’ve had to leave the nursery for 20 minutes and immediately write all the different things I was realizing while sitting alone in a dark room, you’d go, “Well why don’t you just sit alone in a dark room more often and all these ideas will come?”

Unfortunately, I don’t do that, but with a baby you have to do that. Part of me is waiting for her to go to sleep, and that’s when all of these great ideas can come. So, having a baby has changed everything, but I prefer it this way. I think the ideas I’m having are better and richer. And, when you have a baby, movies and stories about babies, children and family are much more impactful to you. They open up a whole new category of emotions for when you’re watching things, which informs how I write as well.

It’s almost like rocking your baby is similar to the times you’re in the car on autopilot and your subconscious mind sort of takes over and runs free.

Pete Holmes: I heard an ’80s Spielberg would have a portable tape recorder in his car and record his ideas while he was driving. It does occupy a certain region of your brain that frees up the creative parts of you.

I’m a big fan of texting myself [while in the car]. I use Siri to text myself all the time. If you’re driving and you press the button and say, “Text Pete Holmes,” and then say the idea…I have so many texts from myself with little things that wouldn’t make sense to anyone if they didn’t know the context. Insane stuff, like how a sociopath would sound.

And then Siri texts somebody you didn’t intend to text.

Pete Holmes: I recently sent an email to myself but Siri messed up and sent it to one of my agents. He was just so gracious. He wrote back, “This is hilarious. Love it.” I was like, “Oh my God, I didn’t mean to send you that.” But apparently, agents are well equipped to just go, “I guess this client of mine is a little insane. I’ll just say ‘thank you’ for this page from your manifesto.”

As a kid, did your manifesto include the pursuit of a career in comedy?

Pete Holmes: I don’t mean to be cliché or sound false but I always wanted to be a comedian ever since I knew it was a thing. I had that right mix. My mom loved me so much—and still does—that it pushed the maximum level [of love]. Almost “Jewish-mother stereotype,” even though we’re not Jewish. She really made me believe in myself very easily. Meanwhile, my father is the kind of guy who goes into a room and changes the frequency to his frequency, a sort of larger-than-life figure.

I saw my dad being sort of like a performer, and I thought if I performed I could really impress him. He also had the right amount of “withholding,” “withholding” meaning I wanted to get his attention. So I had the example of my father—and the need to win him over—and then also had the confidence that my mother gave me by loving me so much and telling me over and over I could do anything.

My parents also sent me to a weird Quaker grade school, one of those private schools where there were no grades and everybody treated the kids like grownups. I remember I had an idea for a class—I wanted to teach a class about a certain type of computer program that I loved to use—and they let me do it! The school was very artsy and forward thinking, especially for the ’80s. They empowered their students.

So I had all of this support [inside and outside the home], and I remember going to the movies as a kid and being like, “I don’t know how, but I gotta get up there. I wanna be on that screen.” It wasn’t until college when nothing else seemed to make sense that I decided to pursue comedy.

I thought I was going to be a youth pastor, which is very similar to a comedian. Teachers and pastors are sort of commonplace showbusiness. They get up in front of groups, they’re entertaining, they’re informative, they sort of make you feel good…so that was in reach for me. But once I got to college and started doing improv, writing columns for the school paper and eventually trying stand-up, I sort of found the confidence to “come out” as someone who secretly wanted to be a comedian.

How much of your current success is a result of being a kid putting out into the universe “who you wanted to be” as an adult?

Pete Holmes: I think it’s been a synching up of a skillset, what the universe wanted and what I had to offer the universe. It just so happened to line up with this dream career. I often tell people, “Follow the dream that’s also following you.”

I talk to a lot of young people who want to be rock stars, actors, comedians – whatever it is—and I’m like, “You have to listen to that feedback from the world.” I don’t just mean if you get a bunch of “no’s” that you quit. I’m saying you need to listen to the quiet voice inside you that receives the feedback [from the universe]. Like, “I’m good at this, I can do this.”

When I was starting to perform open mics in Chicago, me, Kumail [Nanjiani], TJ Miller and Kyle Kinane—all these guys were the best guys. They were doing the best. We weren’t just sitting around going, “I want to be famous and rich because that’s what our culture values.” We were doing it because we were compelled to do stand-up, we had a discomfort when we weren’t doing stand-up, and then when we did, it was received well. That took a lot of work, there was a lot of failure, but we got these little clues along the way, these little breadcrumbs that we weren’t wasting our time.

My wife—for one of my birthdays—gave me a Richard Rohr quote, “The meaning of life is to humbly and proudly return what you’ve been given.” So what I’d been given was a compulsion to perform—something that is necessary for me to do—the skill sets to do it, and growing up at a time and in a culture that values [stand-up comedy]. Those things came together in a pretty wonderful way. When I talk to people who want to pursue comedy who maybe want the love or the attention, I tell them it’s always way more interesting to follow the really deep down drive inside of them, the things you’re given that you can return to the world.

Don’t reverse engineer it like, “The world seems to value this, so I’ll try and figure out a way to do it.” I guarantee The Rolling Stones weren’t doing that. George Carlin wasn’t doing that. Richard Pryor wasn’t doing that. Seinfeld wasn’t doing that. Every comedian I know who started comedy to get rich, to get famous or to get laid isn’t doing it anymore. They weren’t doing it because they had to do it.

I’ve never done cocaine in my life—I never will—but when I do stand-up, that must be what cocaine feels like. It’s energizing, all of my anxiety goes away, it makes me feel powerful, it makes me feel relevant, and it makes me feel seen. And that isn’t everybody’s experience. A lot of people are like, “Oh, I’ve been meaning to get back into stand-up.” I’m like, “Well, what happened?” And they’re like, “Well, I did it for four years, and that was six years ago…” And I’m like, “There’s no shame in saying it’s not for you.” I might be talking to the next Frank Lloyd Wright, maybe that’s your passion. Get some rulers and some drafting tables.

You don’t have to do stand-up just because stand-up is popular right now. Most of us started doing stand-up before stand-up was popular. I started stand-up twenty years ago. It wasn’t that popular. Seinfeld started doing stand-up before there were comedy clubs. That’s why those guys are the best. They did it because they had to do it.

A lot of people fail to see the “breadcrumbs” and end up pursuing careers and other goals because of external forces like expectations from friends, family and society.

Pete Holmes: Follow your dreams, just make sure they’re your dreams. That’s another way to say it. Someone being forced into becoming a doctor or a lawyer because just their parents rode them really hard—that’s no different than someone thinking, “I should be a comedian because I see Comedians In Cars Getting Coffee, and Jerry Seinfeld—he’s powerful and important. I want to be in that car so I can feel powerful and important. But you’re still inheriting a narrative from something outside of yourself.

I guarantee you the people in those cars getting coffee just had to do stand-up. Now, I’m sure there are many people who were talented who maybe quit along the way, but for the most part, the people I know who are doing stand-up, who are writing and who are acting are doing it because there’s something compulsive about it.

In terms of breadcrumbs, was there a defining breadcrumb of success for you early on in your career?

Pete Holmes: Something I spend time feeling sad about and having empathy for are people who have the compulsion but don’t have the talent. That I feel is really, really sad. If someone is reading this and they feel that might be them, I do think there’s a certain extent to which you can improve and work at it and “fake it ‘till you make it” and get it in your bones through repetition. So please don’t read that as “give up,” that’s not what I’m saying. I’m actually a big believer of sticking with it and growing.

There’s a great Lorne Michaels quote, “Show business isn’t fair, talent isn’t fair,” meaning show business is like talent, something given in such gratuitous amounts to Eddie Murphy and very sparingly to others. I’ve always interpreted it that [Lorne] would have loved to be on the show, but instead he chose to follow his talent and produce it. That’s not fair, it’s not unfair. It’s just what is.

I remember when I was starting as an open mic-er I quietly had some doubt. You think, “Am I delusional [for thinking I can do this?]” There’s a thing in comedy called “laughter years,” which is when you think you’re doing well but really not doing well. I still wasn’t quite sure of myself, but Brady Novak, CJ Sullivan and these other guys who I looked up to and admired were at this dinner and said, “When we talk about who we think is going to be next to blow, we think it’s going to be you.”

That little moment of kindness was huge for me and my stand-up. Now, I’m always trying to remember that if I mean something to other people that I tell them, “Hey, that was really funny, that was great,” because—while I think, “Who cares what I think?” People do care what other comedians who are ahead of them think.

Going back even further, I remember doing improv in college and the director—Dan Buck—told me somebody from a haunted house in Salem, Massachusetts was in the crowd and he thought I was incredibly talented and that it might lead to work with him. I was so excited that somebody had scouted me from a haunted house. Even though I never ended up working there, the idea that someone came and saw an improv show and thought that I was talented—it stuck with me.

Pete Holmes Navigates His Way to Comedy and Weed

How did you eventually find your way to stand-up in college?

Pete Holmes: Mark Stevens was the guy who told me to do stand-up. He told me to write and perform. He was the teacher who saw the potential and then watered the potential.

I went to a Christian college where there was no drinking culture, partying, drugs or casual sex. There were exceptions to this, but you really had to go out of your way to find them. So for a lot of college, I was bored. And I’m really glad I was. I’m sort of square and I didn’t smoke pot until I was 28.

Which isn’t to say I think pot is evil, I think pot is wonderful, though I’m a little worried if 19-year-old Pete had found pot, drinking or sex…I was so bored without those things that I had to start doing improv. And then I had to start doing stand-up. It was good for me to be so bored that I started writing things and I started doing stand-up, and once I started doing those things, I started getting feedback, “Hey, you’re good at this, hey, you’re good at this,” and that meant so much to me.

Right, and perhaps you don’t receive that feedback if you’re smoking in your room all day.

Pete Holmes: That’s always the risk. I always think of Bob Marley’s song where he says, “Lively up yourself.” Whenever I get stoned, I’m always like, “We’ve got to lively up ourselves.” My favorite way to smoke pot is to go on Getting Doug With High. I love an audience when I’m stoned because I want to keep the energy going, but I don’t perform stand-up stoned.

I used to be really superstitious that weed was bad for creativity. The first time I smoked I was 28—as I mentioned—and I had an audition the next day for an improv team in New York. I blew it so hard because I didn’t know “weed hangovers” were a thing. Nobody had explained to me that the next day, you might have “cobwebs” or be a little foggy.

I woke up and my anxiety levels were still really low, but I needed the adrenaline to improvise, and ended up having a terrible audition. My teacher and I—Chris Gethard—we didn’t really understand what had happened. I ended up feeling I wasn’t funny for about a month after and I never smoked afterward for quite some time.

Now, for the past ten years or so, I’ve found a good relationship with weed. Meaning, if I do Getting Doug With High, those are some of my favorite shows in the world because weed nudges you to the left and you start looking at things very differently. That’s what people are talking about when they refer to [pot’s] potential benefits to an artist. It helps you look at things in a way that you don’t normally.

If I smoke at home, I’ll maybe write down five or six things. The next day I’ll look at them and maybe one or two of them are okay. The problem is, they all seem brilliant when I’m stoned. I’ve said to Val too many times to count, “I don’t think this is stoned funny, I think this is really funny.” But of course the part of you that’s interpreting whether something is funny is also stoned. So I don’t really trust [weed] as a tool to reliably crank out killer material, but I do think it’s a wonderful thing to help disrupt the monotony of your process.

It’s funny, now I love working with a weed hangover. For some reason, that thing that’s daunted by the idea of sitting down in front of my computer just has styrofoam around it. It’s numb and dulled and life is just less scary. I can wake up and reread that script I’ve been putting off. So sometimes I’ll smoke just to have the hangover the next day because getting weed hungover helps turn down the volume in my brain a little bit.

Speaking of volume, was having your own TV show always a goal of yours as well, or was that simply part of your career’s evolution?

Pete Holmes: I’ve always liked the term “comedian” more than “comic.” Some stand-ups I know love calling themselves “comics,” which I think is beautiful because they really are comics—going up three times a night, they love the lifestyle, they love the culture, they don’t want anyone telling them what to do. We want weird hours, dinner at two in the morning—it’s a liberty sort of person. Nobody can fucking tell me when to wake up in the morning.

That’s a comic. I’ve always enjoyed the term “comedian,” because it means if it’s funny, I want to do it. If it’s writing, if it’s acting, even if it’s producing. Producing is very, very creative, which I think a lot of people don’t realize. If it’s funny, I always want to do it.

With the goal of having a talk show—there’s only like five talk shows—so I think I was smart enough to know that’s sort of setting yourself up for failure, saying “I really want a talk show.” But guys like Jimmy Kimmel knew they wanted to be talk show host since they were 12. I didn’t have that specific dream because I didn’t necessarily think it was realistic. So when Conan came and was like, “Do you want to do a talk show?”

That’s when I allowed myself to be like, “Are you kidding me? This is what I’ve wanted to do my whole life.” And at that point, I was sort of doing a talk show, it had just been deconstructed. I was doing stand-up (a monologue), I was doing sketches (and we did sketches on the show), and I was doing a podcast, which was like the interview portion of the show. So we brought all of those elements together under one roof.

Having a show like Crashing, where it was about me and telling my story, that’s something I’d been dreaming about since I was ten. I used to go into the bathroom—and this was before reality shows—and look in the mirror and do what they would call now a “confessional,” where I’d be like, “Well, that was a pretty weird dinner.

Mom and dad were really going through something. I feel like the mac and cheese made up for it and it’s my birthday in two weeks, so I’m feeling confident I’m going to get that GI-Joe playset.” I really wanted to put on a show, I wanted to turn my life into a show, so [Crashing] was more literally a one-for-one dream come true.

If it’s funny, I want to do it. I never want to stop doing stand-up, that’s sort of like my wife, and the other projects are the mistresses. I just like doing funny things.

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