Pete Holmes has spent decades making people laugh, from his early days idolizing comedy greats like Steve Martin and Brian Regan to his own rise as a stand-up, writer, and actor. In this conversation, Holmes reflects on the moments that shaped his career, the comedians who influenced his style, and the lessons he’s learned along the way. Whether it’s his first time on stage, the evolution of his comedic voice, or his thoughts on the modern stand-up landscape, Holmes shares his insights with honesty, humor, and the kind of wisdom only years in the business can provide.

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Who were some of your early influences, and how did they shape the comedian you are today?

One of my favorite stand-ups is actually Steve Martin, and not everybody knows that he did stand up, usually not a lot of young people, I suppose. And those records (I had them as MP3s) were really important to me,  just for how silly he was, and it really inspired me. But then also when I discovered Brian Regan, I think he is one of the greats, and still is one of the greats. Because I was raised religious and really wanted to be clean, I thought I had to be like Brian and Steve who are pretty clean and then Seinfeld and then Cosby, obviously scandal noted, but then as I matured, I started to get really excited about people that I still love today like Bill Burr and Louie also scandal noted, and every corner of their psyche kind of comedians, which is my cup of tea now.

Was there ever just like a particular moment for you where you said to yourself “I want to do comedy”?

I wanted to be a comedian as soon as I knew it was a thing, and that would have been around Weird Al. I would see people like him and I just couldn’t believe that was his job. But there are two moments, I think for most comedians that I know. There’s when you privately know that you want to be a comedian, but then you keep it to yourself. It’s embarrassing. Obviously you’re not a comedian yet, but you kind of have to declare yourself. It’s like declaring your major. I’m gonna be a comedian, and that’s absurd because if you’re like me, everyone in high school thought they were the funniest person, so everybody thought they were funnier than you, and so it’s kind of weird to say “hey, remember how we hung out on Friday and watched movies in your basement and I was making you laugh like you owe me $15.” That’s kind of a weird thing to say to somebody. So I realized I wanted to be a comedian probably in junior high and then it wasn’t until college that I finally came out as someone who wanted to be a comedian because everybody was picking jobs and if someone was making me say it, I would tell them that I’ve wanted to be a comedian this whole time.

Is there a specific moment in your comedy career that made you realize, “Wow, I’m really doing this!”?

That happens over and over, those are milestones, the first time you feel like a comedian is honestly the first time you do it. It’s a Seinfeld thing. He says the first time you do an open mic, they introduce you as a comedian. They say “this next comedian is coming to the stage”, even though you’ve never done it. You are introduced as a comedian, and you know you’re not good, but you do kind of feel like a seal has been broken and you now are in the running to be a comedian. There was a moment months before I went on stage for the first time. I just read every book I could find. I think nowadays people would listen to podcasts and stuff, but before that you had to read books written by comedians you probably hadn’t heard of, but they were gracious enough to write down what they knew and I devoured and loved all of those. When I was reading those I felt like I was a comedian, even though I had never done that. And that’s a hint at the sort of helpful self-delusion. You need to have a good amount of it but not too much of it. You want to be right in the middle of the bell curve of self-delusion to be a comedian so that you’re confident enough to try it. Deluded enough to think it might work but still discerning enough to analyze and look at yourself honestly when you don’t do well. You need to, you need to be a good mix of honest about your micro progress but also delusional enough to be confident.

Would you say that’s your main piece of advice for someone who wants to become a comedian?

I don’t know if you can choose your level of delusion. That might be something that’s ingrained in you as a child. I don’t think that’s where I would start. I would say if you want to be a comedian, the first thing to do is to recognize that. Everyone that’s trying it is just a regular person just like you, meaning they’re all so insecure about it. You hear stories about Dave Chappelle being amazing when he was 14 years old and some people learn Portuguese in an afternoon. Then there’s the rest of us! You can’t hold yourself to those standards. It’s so much more helpful to go to an open mic. That’s always my advice. If you want to try to do comedy, go to an open mic. And don’t even sign up, just watch. And by the end of it, if you’re like me, you’ll be emboldened to try it because you’ll see that it’s just ordinary people. Just being brave and trying something new. It’s not 15 sensational comedians. It’s just regular folks trying something and then you’ll go, “OK, I don’t have to reinvent the wheel”. You don’t have to be a genius my first time on stage. You can just put together a thematic 3 minutes that’s somehow interlinked and has a beginning, middle and end. You’ll be the standout of most open mics in America, and that’s how I felt. I watched. They’re obviously bad and obviously I was bad too, but when you see how bad it is, you’ll be less afraid to try it.

How would you describe your current comedic voice compared to your earlier work?

At the beginning when I was trying to write jokes I was like, “what’s the employee discount at the dollar store?” That’s an early joke, and I like that. I set up a punchline and make people laugh. And now what I’m doing, I’m really privileged. I feel lucky to have been able to do this for over 20 years. First, I have a strong feeling about it. If I know I feel like I’m working on a joke like my wife ordered a blue apron, and I just think that’s ridiculous. I think it’s so stupid to have your soup shipped to you from Michigan. Like what is this? So I’ll feel a surge of a strong opinion and then my instinct is I can make that funny. I used to be completely uninterested in whether or not I have a strong feeling about the topic. I was just like, well, I could say that and it might make people laugh. Now I’m only interested in things that I feel very, very passionately about, even if they’re silly, and then I worry about the comedy second because you can write that, tweak it, and dial it in. Passion first and funny later.

Comedy can also be about timing. How do you prepare for that in a standup set and how do you gauge the room’s energy?

I completely agree when people say comedians need good timing but what we’re really talking about is hyper listening and it goes both ways. A good audience is very attentive to the comedian, but a good comedian is incredibly attentive to the audience. So when you’re waiting for the next line, you’re really interpreting the sound an audience is making. Are they ready? and it can be funny to say something before they’re ready. Sometimes usually it’s a little bit more like music where they’re establishing the tempo. Timing sounds like something intrinsic in the comedian. I would actually say the skill is better labeled listening. The comedian has good instincts and can interpret the sounds and audience makes. That’s what I really think a bulk of my craft is, is interpreting the sound and the energy of the crowd. They might tell you, be “rough with us”, meaning like, “make fun of us” or “we’re so bored and complacent, please just shock us out of this”, but they might be just absolutely delightful and they’re flowing with the set.

Is there one comedy myth or a stereotype that you’d like to debunk for people who might not fully understand what being a comedian is really like?

I would like to debunk the very modern belief that the comedian wants you to talk to them. You just get people participating, and that’s because of Instagram, and I have a real chip on my shoulder about Instagram in particular. Most comedians don’t want to post clips of their material. They want to post clips where they’re talking to the audience. So it seems like 80% of clips of stand-up are the comedian engaging with the crowd. And great, I’m glad you didn’t burn the material, but you’re hurting the art form. I’m not even asking comedians to stop doing this. I understand that they have to do this. I’m very lucky that I have lots of specials and I can cut those up and put those on social media. If I was starting out, I would put up clips of me doing crowd work. The problem is, crowd work sucks. Some people are amazing at it and I’m saying I don’t like it. It’s not for me, it’s not what I do. So when I go out and do stand up and someone just starts answering a question that I asked, I don’t take it as hostility, it has the illusion of a conversation, but really I’ve prepared something. I’ve rehearsed something and I’ve prepared it, and if you let me drive the car, I promise you’re involved with your laughing, when you clap, and when you don’t laugh, you are in. You don’t have to verbally tell me what you think about each premise, and that’s the downfall. Social media is so useful to us for selling tickets and keeping in touch with our fans, but it has the risk of degrading what stand-up is. A lot of people are going to think, “I can’t wait to tell this guy what I think”. Sure, but there’s 600 people here. We need to just surrender to what it is. I’m not dragging people that do it. Some people are brilliant at it. But when I go to a comedy show, I don’t want the comedian to look at me and say, “what do you do?” I don’t want that. Like a magician, I don’t want a magician to say, “what do you think should be in my hat?” I want him to say I’m going to pull a rabbit out of my hat. That’s a show. And now because of social media, people are like, “I can’t wait to tell this magician what he should do”. Let the magician do magic that he prepared at home and thought about and sculpted. Gary Goldman has this great line. When a comedian asks the audience, “what do you do?” I always want to say, “what do you do? Like do comedy, do your job”. I don’t watch Severance and have Adam Scott look at me and say, “do you think I should do it?” I don’t want to do that. I want to be entertained. I just want to laugh. Please do what you do so I can laugh. Don’t interview me badly from the stage.

You’ve made such a huge career out of just making people laugh. What’s one thing that always makes you laugh?

There’s a podcast called Valley Heat that I am obsessed with, and you should look, when people recommend podcasts, they’re like, like, why are you giving me this assignment? It’s like such a dumb thing to do. Like I’ll find my own podcast. Thank you very much. But with Valley Heat, I scream laugh at it. I didn’t know something could be so funny and it’s just a guy talking about his life even though it’s made up, it’s very, very funny, kind of like Tim Robinson. Tim Robinson also makes me laugh. I also do like what people call good bad movies, like movies that are so bad they’re good. And there’s Neil Breen! Those really, really make me laugh very, very hard and no disrespect to Neil Green, who I think knows that people find these movies and now make them for that reason.

You have such a well loved podcast, ‘You Made It Weird’, where you’ve had such a diverse range of guests. This is a hard question, but who has been your favorite guest so far and why?

My podcast is so blended with my life, meaning it’s a podcast to the audience, to people who consume it as a podcast, but to me it’s like how I’m spending my days. It’s conversations I’m having with interesting people, so it’s not dodging the question when I say almost always my favorite episode is the one I just did, because that is the most updated version of me. That guy is talking about the issues that I have right now. If I listen to an old episode, don’t get me wrong, I love some old episodes. Jenny Slate comes to mind as one of my all-time favorites. but I like the ones where I’m like, “that’s me now”, and a lot of times we’re like figuring things out, like things with my family or things with work or things that are stressing me out. So it’s a very useful podcast to me,, but that being said, you can’t beat Gareth Reynolds, Jenny Slate, and Josh Rubin. These are just some of the funniest people in the world. And then when it comes to useful ones, useful meaning like things where I really had my mind blown or learned a lot, I remember John Vervay and Richard Roar being really great, some of these bigger, bigger thinkers that have really shaped my perception of reality. So it’s both. It’s people like Jenny that make me laugh really hard and then it’s people like Richard Roar who reframe the fundamentals of reality.

Are there any new exciting projects that you’d like to share with us?

It’s interesting being a comedian, that also acts, writes, and produces. It’s a little bit like being an emergency room doctor or maybe a firefighter or something, meaning that there’s a lot of downtime and then all of a sudden someone’s in triage and you’re in the middle of a project. So I’m in a place where right now we’re waiting to hear about a slew of things, but nothing that I can share. So I’m a doctor in scrubs drinking bad coffee and things are pretty chill right now. But right now it’s touring and it’s the podcast which are the two consistencies in my life and I’m really grateful for both of those like my Vancouver show obviously and a lot of other shows coming up that are all on my website which is peteholmes.com.