Pete Holmes on Making it Weird, Origin Stories, and His New HBO Series Crashing

I’m what you might call an aimless walker. I find destinations heavy and irrelevant, distance too. Each trek is accompanied by a soundtrack, and for a long time now the background music to my purposelessness has been You Made it Weird with Pete Holmes. 

For years, Holmes has been sitting down to long conversations with comedians, some actors too. Some his closest friends and others he’s never met before. Regardless of their stature in his life, he and his guests open up like two old friends at the end of the bar. Nothing is off-limits and Holmes is quick to share the most intimidate details of his life. Now, that almost therapeutic riff that he’s found is taking on new form in his upcoming HBO series Crashing. 

I was eager to talk to Holmes as a fan and curious observer of his life over the past few years. We spoke about the birth of Crashing, which is directed by Judd Apatow, where Pete Holmes the character meets Pete Holmes the person, and what it’s like to devote yourself to a career with a penchant for punching its subscribers in the face. 

Here’s how that went. 

Do we make it weird now? Is that how this works? 

[Laughs] To really make it weird you have to talk for at least 90 minutes at the point the guest wanted to leave.

Don’t worry, I’ll fit it in somehow. 

Perfect. 

At this point, I have seen the first six episode of Crashing, and I truly love it and think it’s amazing. And I have been an avid listener of You Made it Weird for years now, so I know that the show is really pulled out of your life. How is that for you? Acting out your life? 

Yeah I know. It’s kind of everything. It’s cathartic and other times it’s a little bit overwhelming. It can be very therapeutic, and then other times it can be like an episode of Twilight Zone or something.  

But it does kind of give you a little bit of a zoomed-out perspective on the drama of your life, and I mean your real life. If you can recreate it and laugh at it, it doesn’t seem so big and scary. Something like a divorce or dealing with boundary issues with your family, or whatever it might be, seems so important and real at the time and then when you make a TV show, that’s pretty close to—at least emotionally—how it felt it is interesting to be like, “oh this was all just kind of a joke,” and that helps me. It helps to give me perspective. 

With that said, a lot of times on the podcast you equate it to therapy. You are very open and honest, sharing a lot of deep thoughts and experiences and talking them out one-on-one with your guests. So how is the experience of knowing that now some of the most intimidate details of your life are going to be played out for hopefully lots and lots of people to see? 

It’s kind of like I’ve been in the minor leagues. I’ve been dabbling in telling a lot of people on the podcast the secrets of my life, my insecurities, or sharing some of my pain. Now, if the show does well—which we are all hoping it does—you are absolutely right, a lot more people are going to see it. In fact, that’s already starting to happen. My parents, thankfully, don’t listen to the podcast but they have seen promos for the show, and the same goes for some of my cousins and stuff. You start having to catch these people up on the idea.  

I’ve been doing this for years, the idea of sharing every secret, every detail. It’s probably weirder for them than it is for me, they have to play catch-up to this strange lifestyle of sharing every thought and insecurity you ever had. So I guess I’m okay with it, I’m excited about it because I think living and honest transparent life is a great life to live, but we will have to wait and see how some of my family and some of my friends are about it. 

I didn’t even think about that. But if they don’t know it’s a whole new world for them. Like opening your diary and letting them in. 

Exactly, and then I have to be like, “my diary has been open for many years now!” [Laughs]

Hey ya missed it! 

Yeah! Now they just have to catch up. 

Now with Crashing, you are playing Pete Holmes the character but you are a person that is past those events already and going in with knowledge that the character does not have yet. Do you have to differentiate between those two people, is it difficult?

It’s gotta be easier to go backwards than forward with intelligence. Like if I had to pretend to be some sort of doctor and I had to learn all this jargon that I don’t actually understand. I think it is way easier for me. 

I carved out this nice role for myself where I sort of had to think about who I was when I was twenty-two, and I kind of like being that guy. It’s fun to remember what it felt like when you were super naïve. When you had never smoked pot. Never gotten drunk or anything like that. Just being a sweeter, friendlier version of myself. Everyone kinda likes to be around that guy anyway. There’s those other shows where you have to play some kind of jerk, but I get to be a likeable character, and it’s also someone I was. Real Pete, grown up Pete, who I am now, hasn’t been around as long as sweet naïve Pete. So it’s almost even more familiar to pretend to be him again, and it is actually quite fun. 

Speaking of sweet naïve Pete, the show takes a really different slant on the comedian lifestyle. Pete on the show is this very sweet polite guy with none of the vices that comedians are known to have. Like you say in Crashing, you just want to tell jokes that make people happy. Was that true for you, real Pete, coming up? Did you find it harder to be on that straight-edge curb outside of the “normal” comedy life?

Well, yeah. I think that is one of the interesting things about stand-up. Some of the things that make it harder at the beginning are ultimately the things that make you stand out. When you are starting comedy and you don’t do jokes about sex and you don’t have any crazy experiences about sex or drugs or anything like that, and you are following a lot of comedians who are making dick jokes and stuff like that, and then you have to go up and talk about refrigerators or whatever, it’s way harder and you feel that temptation to adapt and change. 

I think that’s what’s interesting about the show, it’s a guy who doesn’t really want to change and wants to stick to who he is authentically. I am hoping for him as a character, that’ll pay out. I know a lot of people who start out and we stick out like sore thumbs and it’s kind of bad. But then eventually, that thing is what makes them shine. 

Now that I’m a few episodes in, I can see that. I can also see how it’s not just a battle of making it but also a battle to fit in, or at least exist in your own personal way in this bigger world of comedy. 

TJ Miller has that great line where he says, “Part of being an opener is being a good hang.” You start to realize that the job is one hundred percent of you. You need to make friends, you need to fit in, you need to not be a jerk, and you have to be funny on stage. There are a lot of worlds to navigate. 

I also think it’s interesting that people who aren’t super comedy nerds or stand-up fans, you can easily pour your own ambitions and your own aspirations into a comedian. I feel like comedians are just the base level of what anybody wants no matter what their pursuit is. For example, if you want to be a writer or you want to be an architect, or you want to be a cook, whatever it is, you want what’s inside of you when it comes out to be greeted in a positive way. So stand-up is really susceptible for people to project whatever way they relate to it on to it. 

There’s something interesting about how it consumes every aspect, where living is as much of the job as the actual job is. You talk a lot about the comedian brain and how it is always going except when comedians are on stage doing their time. Do you feel that same relief when acting, especially playing yourself where your psyche is the thing you have to marry? 

It’s funny, you reminded me of something Artie [Lange] says in the pilot, where he says its not just about being on stage it is this whole lifestyle that is pointing to you being on stage. But the truth is, even if you are a headliner, there’s still twenty-three hours you are not on stage every day. There’s a lot of bookkeeping, emotionally speaking, to stay healthy and to stay sane in kind of a strange world, and that’s one thing. 

The other thing is that, the reason I like calling myself a comedian and not a comic is because I kind of get my itch scratched from all different types of performance. Acting is certainly one of those things where you do it all day and the time really flew. That’s how you know you are doing something that’s challenging enough to be interesting but then also fun enough to really be able to get lost in it and enjoy it. 

You talk about how your “comedy origin story” comes from a place of wanting attention, that’ where the satisfaction comes for you. 

Yup. Sure. 

You have had your hand in so many things: writing, commercials, voiceovers, sitcoms, writing, talk show, and of course the podcast. Now you have this show, is it the natural progression of where your life and you career are at this moment, or  did it develop out of doing the podcast for so long with the spotlight on your life? 

Well the talk show got cancelled and I was in a place where I felt very stiff. We were doing so much comedy and then it got cancelled and I didn’t have anywhere to put the energy. I knew I had to find a new vessel for it.  

Initially, I thought we should do a sketch show or some sort of interview show. Those were elements from the talk show that I really enjoyed. Then I just had one of those moments where I was like, “what are you really here to do? What is the story that connects with the most people? What will have the greatest impact on people’s lives? What is that story?” 

Then I thought oh it’s the story of a guy who marries his first girlfriend and she leaves him for another man and then he starts doing standup. That’s what is written on my stone, that’s the story that I inherited. So more so than a sketch show, or an interview show, this one feels uniquely me. We’re all gonna die, I’m gonna die, and what would I like to do before I die? [Laughs] It was tell this story. 

When I thought of it, it just rang out like a Judd Apatow story and that was very exciting to me. I met him a couple of times. He had 15 minutes one morning so I flew to New York just to meet with him for 15.  It all kind of hit me at once, not like what can we do, but what should we do? What is the next logical step in your own evolution, and that’s the answer that I got.

It’s good when it comes to you like that, it’s your release and your legacy.

It did happen quickly. But now that you are making me think about it, it did happen slowly because of the podcast—which has been on for three years maybe—was really teaching me how to talk about emotional things while being funny. So it was probably cooking somewhere deep in my subconscious, but the moment that it sprung up did feel like some sort of revelation. Like “oh then every episode I’m staying with another comedian!” It seems like a TV show, but a TV show that is true and has some heart and can be really, really funny. That’s exciting. 

For someone like me, who has been listening to the podcast for so long, and now watching the show, it was definitely and, “oh duh” moment. This was the clear progression. Seeing all those comedians in the show it’s like, “oh yeah! This is it!” 

Yeah exactly! I feel very lucky. Something just objectively interesting happened in my life and it even had this twist with the comedians. It was TJ Miller. It was John Mulaney and Nick Kroll and all this guys that really caught me when I fell and we weren’t even that close yet.  To be able to take that story, and it’s a good story to tell, it’s a story that has some redemption in it, it has some hope, and it has all these really funny comedians. I was like wow I lucked out here. 

The show starts off with your marriage ending and you throwing yourself into trying to make it as a comedian. It’s a tough start, to say the least. I don’t want to give too much away, but there is a moment where it feels like some sort of relief. I don’t know how much that lines up with your life but was there a moment that you felt that you are out of the rut and the coming up and you’re just doing it?  

Yeah. That’s another thing that Judd does really well. He takes these quiet internal moments, like the moment where you feel that everything is going to be okay, and then we blend that with the story of whatever it may be.  I don’t want to spoil it either, and you can determine what to keep in. You and I are kind of at the warm-up.  

I remember the moment I thought I was going to be okay was the first time I did this club and they gave me twenty minutes—an unheard of amount of time—and I got up there and behaved like a headliner. I couldn’t really out my finger on it, but there was a claiming of the role. When I got off stage I felt like I just got my head above the clouds for just long enough to really cement in the idea of me being a comedian. 

But on the show, we take that sort of feeling and merge it with a good story so we have the best of both worlds. The truth is that I was in List, Illinois in a conference room in a Holiday Inn that they put black curtains on the wall for the weekend so I could do standup. 

Well there’s that. Which was good for you, but not the most ideal circumstances, and in the show for that quiet moment where everything is going to be okay there are a lot of moments where everything seems terrible. For instance, all the barking, which just ate my heart out. Is that the worst thing you ever had to do for some time, or is there something else you’d like to share?

I think that’s what’s interesting about comedy. It never really stops. It does get better, it stabilizes. Around the ten-year mark it can start to feel a little bit more secure, for sure. But, when I look back I think barking was really terrible but it was the barking that led to college shows. That was the first thing I did that I was making a little bit of money, making a living. Then the college show leads to a standup show with no microphone in front of an active elevator. It’s just suffering to get to the next level of suffering and that would take you to some sort of cruise show or corporate show or maybe you’re an MC for a liquor that’s hosting some event at a bar.  You are always doing these really interesting strange side jobs and that to me is where the comedy lies. That’s where the juice is. To stick in that zone where it’s not quite as bad as it was but still interesting. 

The hustle. 

Exactly, the hustle. I like origin stories, like you said. It is so much more interesting to me when Bruce Wayne is sewing a Batsuit than when he is just fighting Mr. Freeze or whatever. I like finding out why people have the grip and the endurance to stay in a thing that keeps kicking them in the face. That’s why in the pilot so many people are telling Pete to quit and so many things are going wrong, and that’s not because those things actually happened all in one day but they do happen. That’s what it feels like to start as a stand-up, and I am happy that I kind of get to represent my people, meaning comedians, and hopefully delight and entertain the audience as they see what a literal adventure it is with highs and lows and big wins and big losses trying to become a standup is. 

Crashing definitely shines a light on all of that, things that I don’t think most people could even begin to venture a guess on. 

I am glad it comes through. So few people have seen it, so it is always nice to get some feedback, I really appreciate it. 

Thanks for speaking with me. I really appreciate it. 

Thank you, it was my pleasure. Thanks for listening to the podcast too, I appreciate that a lot.

Crashing premieres on Sunday, Feb. 19 at 10:30 pm on HBO. Also be sure to catch You Made it Weird available through iTunes or on Nerdist.com.