Talking to Pete Holmes About Standup, Writing, Podcasting, and the Joys of Being Made Fun Of

For any non-comedy nerds out there who might be reading this, standup comedian Pete Holmes is the voice of the E-Trade Baby.

OK, got your cultural touchstone? Good. Because you should check out more of his work.

Holmes is kind of a comedy renaissance man, dabbling in cartoons (The New Yorker), sketches (CollegeHumor, etc.), sitcom writing (Outsourced), acting (Ugly Americans) and podcasting (“You Made it Weird”) to supplement his work as headlining comic. He’s become a major draw on the standup scene, and recently received a Best Club Comic nomination for Comedy Central’s upcoming Comedy Awards.

Fans of “You Made it Weird” know that Holmes loves to talk comedy, and I got a chance to experience this firsthand last week while he had some downtime. We talked about his start in comedy, why he decided to get rid of his notebook, and his fondness for being ridiculed.

What’s a day like for you when you’re not touring or doing your podcast or working on other projects? Do you ever try to find time to try and catch your breath?

Yeah, I suppose I could appear busy, and sometimes you are. Sometimes I liken the comedian’s lifestyle a little bit to a firefighter’s in the sense that there’s a lot of waiting and a lot of nothingness. And then there are moments of urgent firefighting. [Laughs.] I’m not comparing the nobility; they’re risking their lives certainly, but just the schedules, just the idea of sitting around and waiting for the bell to ring. There’s a lot of down time in a good way. You can carve out time to go hang out with friends and see movies and stuff, and I think that’s really important because if my life was all just touring and stand-up and meetings and whatever, I would be leading a very unrelatable and not very funny life that nobody really wants to hear about. I think you need to live a life worth commenting on. I’m quick to take road trips and even cancel some shows just to have dinner with friends because that’s where the bits come from. [Laughs.] I just want to be clear: I go camping and I’m not trying to get material out of it, but there is a quality to relaxing your brain and having a good time, and sometimes something really funny will slip out of that.

No notebooks on camping trips. Got it.

No…That scrounging-for-bits thing kind of ends about, I don’t know, maybe 10 years into doing comedy. It’s much more relaxed. We can all be more adult and more like people and less like ravenous, comedian-types who only think about comedy.

You do a lot in terms of web videos, sketches, standup, cartoons, writing, etc. Can you ever take your mind off comedy or are you always thinking of new ideas for various projects?

Comedians are privileged in the sense that what we do to recreate is what we would do to work as well. The biggest idea of a good time for me is making the Batman videos that we did. That is my ideal day. That is exactly what I want to be doing…I like doing cartoons. I like writing things. It’s fun for us to let our brains light up at the thought of a TV show, or the thought of what could be a movie. That’s intoxicating and really enjoyable. There are days when I want to do no thinking whatsoever. And no talking whatsoever, and no sharing. And I do that kind of all the time. I think at least one day a week I will hermit it up and not talk and just not want to listen to anybody. It’s not depressing; it’s actually lovely. [Laughs.] It’s a lot of recharging. But the rest of the time, what I would do for fun, is what I do for work. And I’m very grateful to be able to say that. It makes me feel very lucky.

But back to your question, the idea of doing a lot of different things is there’s like seasons to stuff. I can’t mark it down, I’ve never tried to see if there are literal calendar seasons to them, but there are just times in the year when I feel like doing a shit ton of standup, and then there are times when I feel like doing less standup and more sketches. You try and develop this system where you have enough activities, and they’re all under the umbrella of comedy, and if one of them isn’t being exercised at that moment  — let’s say live performance — then that’s when you can kick it in your apartment and try and write a script and or try and come up with an idea or something. It’s kind of like leaky buckets or something. It’s all comedy, but different things come to the forefront at different times.

Now is it easier that way? I hate to use the word compartmentalize, but do you find yourself being more productive if you focus on one thing at a time, such as standup, or writing scripts, as opposed to having a melting pot of different ideas?

That’s an interesting question. I think it really depends. Sometimes, one thing will feed into another. When I was writing on Outsourced, the days that I had a set the night before were better days. You might think it was good to stay home and go to bed early. But really the truth was if I went out and did a couple sets, the next day I would be running on the fuel of the affirmation and the connection of doing live standup, and I would come into the writer’s room carrying that momentum. There are some times when bouncing from one thing to another and switching gears is invigorating. And then there are other times when you’re like, “I am just not interested in that right now.” I would go through huge periods where I just didn’t feel like doing any single panel cartoons when I was doing that. I just couldn’t force it and I don’t think you should force it. I think you should go with the one that seems to be calling your attention the most. It’s a weird thing. It’s hard to control the things that are going to inspire you. Really, we’re all just at the mercy of our subconscious. And sometimes our subconscious is just lobbing us really great jokes and we write them down. And other times it’s just not; it’s just taking a break. And you can’t be mad at it. And that’s when you take a couple days off.

It’s hard to trace your start in comedy. I know Boston is involved, Chicago is involved, New York is involved. When did you first get up on stage?

That’s a good question. When I was in junior high, I went to a really hippy dippy Quaker school where we called our teachers by their first names and stuff.

I’m all for that.

Yeah, they let me teach a class. [Laughs.]

I did plays and stuff but in 6th grade I started going to this camp called Friends Camp and we started playing improv games and that’s when I realized “Oh, the point of this game is that we’re supposed to be funny?” That just blew my mind…Then I started doing improv in high school and when I got to college, I started an improv team — this was in Boston — and I started writing a humor column and started drawing cartoons for my newspaper and that’s when I first got the idea that I wanted to be a comedian. That’s when I first admitted to myself that that’s what I wanted to do. Everything seemed to be pointing to that, but it takes a strange type of courage to admit to your friends and family that you think you can be a comedian. I started doing standup my junior year of college…When I graduated I realized I wanted to be a comedian and I was like “I’m fucking done half-assing anything.” Once I found comedy I decided that was what I was going to do. No backup plan…Even though I was doing standup, I decided to stick with improv because improv felt safer. I thought if you’re going to do improv and if you want to be on SNL, what you do is you move to Chicago. That’s how I wound up there…And it’s insanely bizarre because Chicago is supposed to be this improv and sketch town, and what I ended up stumbling into, and I’m so grateful that I did, was this amazing under-the-radar standup comedy scene, and that was where Kumail Nanjiani and Kyle Kinane, Matt Braunger, John Roy, T.J. Miller, Robert Buscemi, Hannibal Buress all started at the same time — just a really great group of people. I was in Chicago for 3 years, and with that “not fucking around” new motto that I got after college, I decided to move to New York, because that’s what you do if you want to do standup. In 2004 I moved to New York and lived there for six and a half years. Once I felt like I hit the ceiling there — I had done my half-hour, I had done Fallon, all that sort of stuff — and made the friends and connections I wanted to make, I thought “OK, now I’d like to act, I’d like to develop television shows, I’d like to create,” and again, going with the “not fucking around” model, I moved to LA.

And in Chicago, you got your start at the legendary Lyon’s Den?

Yes, I would get off the train and I would walk past this place and on the marquee there it said “Monday Comedy.” I didn’t even know what that meant. I would walk past it and it was kind of like taunting me. I knew I wanted to do standup but it’s a fucking difficult thing, and it lasts a lot longer than you want it to — when you want to be a comedian and you’re not good yet. [Laughs.] It lasts years and years and years and years. That’s what separates the wheat and the chaff sort of thing. It’s hard to get through that time. That’s why comedians have that instant bond and the camaraderie because we know the absurd pursuit of wanting something and the requirement of being bad at it for a while. So I would see that Monday comedy sign and I would be afraid of it. It would make my heart race. I didn’t want to look at it, because I knew that that’s where I had to go. And I knew that it scared me…Eventually I went in and I watched the other comedians and that really put a fire under me in a healthy, not prideful way, that I could do as well or better than these people, not the best people, but some of the bad people. So I started doing that and then very quickly, I could start performing 5 nights a week, and that lined up with my good comfortable drive and that calmed me. And eventually, I could see the progress…That’s when the improv started to fade away.

I’ve heard you say you don’t write material down anymore.

Yeah, and that was something I used to think was preposterous.

Yes, that’s difficult for me to wrap my mind around. You talked about it on your podcast with Bill Burr.

The idea of not writing your material down is to talk about things that you know your perspective on. If you were to tell a story to me about something that happened to you, you wouldn’t have to refer to your notes. We’re trying to write material that is so ingrained in our perspective that why would you have to look at a piece of paper to tell you how you feel?…The whole goal of the first 10 years of stand up is to figure out what you care about and what you can be funny about so much that you don’t need to memorize it. If you’re dictating, the material is coming from I think the right side of your brain. If you’re just talking and you don’t necessarily know the exact wording of what you’re going to say, now we’re in the moment, now we’re in the left side of the brain. We’re being creative and being present. And that creates a certain electric standup that I don’t think you get with the presentational style.

In terms of everything that you do with your writing and the sketches and the podcast and standup, etc., what’s the most fulfilling for you?

I’m very happy to say it’s a three-way tie between standup, which is the obvious answer. But standup can go the other way so often. Like it loses a little bit of its luster when you just get back from two rowdy Saturday night shows where the crowds were just really drunk and not paying attention. It loses a little bit of its edge because of the inconsistency factor. But certainly standup, and then it’s a tie with doing my podcast and doing the sketch videos that I do with Oren (Brimer) and Matt (McCarthy). They’re pretty similar. The podcast is the closest I get to really feel like I’m creating something artistic. I know that’s a little bit pretentious to say, but I’m just talking about the art that I would like to see.

Was there much of a learning curve for you when it came to hosting the podcast? Did you have to develop certain skills?

Yeah, I look back at the show and it hasn’t changed that much, but a couple things have changed. Like with the first episode I did with Kumail, I wrapped it up in an hour, and it didn’t feel right at all. We had a bunch more to talk about, but I thought podcasts were only supposed to be an hour. Now the show is almost always 90 minutes or sometimes even two hours because all I want to do is have good conversation. The real thing that I had to get over was the awareness of the audience that’s going to listen. I almost forget that people listen to the show. When I first started doing it I was urgently trying to make it funny and urgently trying to make it interesting, and then over time, I think I started to calm down a little bit. I started to be more like, “Let’s just let this happen.” I just don’t want to try. There’s nothing really funny about trying. By virtue of the style of the podcast, it’s going to be me being me and it’s going to be the guest being the guest with me. And then that’s going to be the show. I mean don’t get me wrong, I try hard, but I stopped “trying.” Do you know the difference?

Does that mean less preparation?

That’s interesting. I have a piece of paper with a bunch of facts about people written on it and some questions, and a good podcast is like a good standup set in that I don’t look at the paper.

How did you get on the Nerdist network? Did they come to you?

So, just like anybody, I’m aware of podcasts. Also, like a lot of people, I was like, “That sounds stupid.” [Laughs.] Why would I want to be another voice in this sea of podcasts? And then I started listening to Marc Maron’s podcast and I had that phenomenon of wanting to interject and wanting to participate. And then what really sealed the deal was Marc telling me that doing the podcast was the closest thing to standup for him. And then with absolutely no urgency, not knowing that there was some urgency because Nerdist was about to close the door and say we have enough podcasts, I started kicking around ideas. Originally I was only going to talk about religion — I’m really glad I didn’t do that. I realized I change enough in six months that I needed a podcast that’s allowed to change as well. I’m sort of a doofus that way. And then I came up with the title, and thought what if I just do what Maron’s doing and I call it “You Made it Weird” and I try to have weird honest moments that you wouldn’t have on other shows. I almost called it “Keep it Crispy”…My manager is worth what I paid him this year just because he said “don’t call it ‘Keep it Crispy.’”

And now you’re doing “You Made it Weird” live?

Yes. I wasn’t really planning on doing a live one, but once you have a podcast with a decent amount of listeners, I think it’s just kind of a natural progression that people ask you to do a live one. I have the benefit of again, copying what Marc does. The first one is going to be four short interviews, and then we’ll all mess around together, which I think is going to be a lot of fun. The first one is April 7th and will have Michael Ian Black and Jim Gaffigan and Matt McCarthy.

You really seem to enjoy when your friends make fun of you on the podcast.

Yes…I think it’s just growing up with an older brother who gave me a lot of shit, you know, an appropriate amount of older brother shit. When someone makes fun of you, they have an intimate knowledge of you. They know who you are and what you’re about, and it feels good to be understood. If someone points out some bullshit contradiction or shortcoming in my life, it delights me. If Marc Maron makes fun of me for not touring enough, I mean how great is that? I’m like, “He knows something about me!” I think that’s what’s happening there. It concerns me a little bit, especially in the Maron one where I felt like it was bordering on masochistic how much I was enjoying it. I would just like to go on the record that I’m not kinky that way. [Laughs.]

Pete Holmes will host a live “You Made it Weird” on April 7 at the Gramercy Theatre in New York. For tickets, click here.

Phil Davidson also likes it when people make fun of him. Except when his mom does it. That gets old and isn’t very productive.

Talking to Pete Holmes About Standup, Writing, […]