“People always say ‘It must be weird that I know so much about you.’ And I always say ‘What’s weird is I don’t think it’s weird.’”
When he steps out onto that stage, there is a certain characteristic that can’t be described. All negative energy, any bad day you were having, just gets sucked away. It’s something infectious. You can’t be in a bad mood at a Pete Holmes show. His exuberance and wide-smile will take care of all of that for you.
Pete Homes second HBO special, Dirty Clean, is as fitting a title as there is. If you were to ask someone who takes pride in being clean, they’d call him dirty. If you were to ask someone who prides takes pride in being dirty, they’d say he’s clean. This is the middle road Pete travels down. He is neither one nor the other while somehow remaining both at the same time. There’s an all-encompassing nature to him. He is the kind of guy who can be enjoyed by seemingly everyone.
In a world of Netflix, Amazon Prime, Comedy Dynamics, and all those other streaming giants that has been bringing stand up specials directly to us at a rapid rate, there is something to be said for the nostalgia factor of an HBO special. There was a time when having an HBO special was the biggest crowning achievement one could possibly hope for. Starting with Robert Klein’s first HBO special in 1975 and continuing with a slew of George Carlin specials, HBO was once a mecca for comedy. This is something not lost on Pete Holmes going into his second special with the network.
“Well to me, to have it on HBO is special,” Holmes tells us over the phone from Los Angeles. “I don’t know if it’s just me, but when I think about [Gary] Shandling and all of the people that have had HBO specials, it still feels very unique and privileged and an honor to be on that network, because there are fewer of them to be honest. There are a lot of places you can go obviously these days. There’s an inundation of comedy specials that we all experience. Netflix is releasing like 75  specials on New Year’s Day. And I think there’s just something about HBO. You go to HBO Go or HBO Now and there’s just a highlight of the two or three specials that are current or new. And that is a very coveted position as far as I’m concerned and it’s something that to me is an honor to be in that small sort of group.”
This past year has imaginably been crazy for Pete. 2017-2018 alone has seen him getting married, the birth of his first baby daughter, he is starring on the hit HBO series, Crashing, and he still finds the time to release new episodes of his hugely successful podcast You Made it Weird.
There is this tendency in people, the higher up they get spanning different vehicles throughout their career, to maybe just focus on that one thing. To juggle everything would be too hard, and might lessen the quality on top of it all. But Pete Holmes is proof that it can be done, and flawlessly at that. Even in the midst of everything else, somehow his stand up has never been better.
“I always look at stand-up as your wife, and any other sort of project that you have as sort of a mistress,” he tells us. “It’s like some side thing you have going on. Not to say there’s any less value in that, but you kind of have to stick with your wife through it all. It’s your first love for a reason, it’s the most direct relationship you have with your audience. It’s literally just you and them, with very few other voices weighing in. So it sort of stays the purest and truest way to directly entertain your fans. So I’m a big believer in staying in touch with your stand up, even when you don’t necessarily need to.”
He continues: “Although in my case, stand up and being in the world of stand up and remaining a guy who goes out to the clubs and sees the community, as silly as that might sound, it’s really important to me to stay in touch with comics. How comics talk, how comics feel, what comics are talking about. And that informs the show, never mind the idea that my character on Crashing, obviously, is basically me and is trying to get good at stand up. And in the third season there are more and more instances where my character has to be good at stand up. So to do that I have to remain good at stand up. And it really is the only art form that I am aware of that if you don’t do it for three weeks, you sort of forget how to do it.”
As he steps out onto that stage, it is seeing an old friend. He even calls his fans “Friends that I just don’t know.” That is just his charm. He connects with you. You’re no longer a part of a larger picture as an audience member. It’s essentially just you and him (but please don’t take that as incentive to try and talk to him during the show).
There’s this feeling of intimacy within his act. His act deals with things such as what he’s learned now that he has a daughter, his hot air balloon proposal, why it’s a good thing his dog can’t text him, Elon Musk, and the afterlife. But there’s also this moment in the show in which he asks everyone to sing Happy Birthday in their head. And he stands onstage in silence as he waits for everyone to do it.
These are the type of things that would just get lost in a larger room. “I understand why some people want to do Madison Square Garden, for example, or enormous venues,” he admits. “For me and what I’m going for is a little bit more of an intimate connection with the audience. Because I think you can feel that and I think it makes you perform the jokes differently. Because if there’s 50,000 people there, you’re just going to give it so much energy and so much pizazz. I don’t know what the Aladin Theater [where he shot the special] seats, but if it’s under a thousand, you can really take your time and be a little more natural. I get a little strained if there’s thousands and thousands of people there. And I like comedy specials that have a natural ease to them. So that’s why I try to pick venues that are closer to what I would do if I were just passing through town.”
In addition to what theater you choose, so much of whether or not you have a good show relies on what city you choose. And if you want to have a truly great stand up special, you need to pick a truly great city that reflects that. These are the thing that most of us wouldn’t really think about, but for a comedian, location can make or break a show.
“So much of where I do a special has to do with honestly how I feel when I’m in the city,” Pete tells us. “It’s almost like it’s not just the audiences. Obviously Portland has a great comedy audience, they’re a sophisticated audience. I think they’re with it in that way that you want them to be. They sort of have their finger on the pulse of the tone of comedy these days. But it also has to do with where do me and Chris, who opens for me, just love to go? Because stand up isn’t just one hour of the day. You have 11 other waking hours usually where you’re going to be eating and talking to the people and walking around. And I just for some reason love Portland. It’s like a punk rock train set if that makes sense? It’s got rock and roll to it but it’s also very cozy. And that’s kind of exactly what I want to feel leading up to a show.”
The typical audience for a Pete Holmes show is a lot of die-hard comedy fans, but they’re also fans of his podcast, You Made it Weird. There’s a weird connection all of these fans have with Pete. Given that his podcast episodes can run anywhere from 1 hour to 3 and a half hours depending on the guest, there is really that sense of “I know this guy!” These are people who know Pete inside and out, are as loyal as being joined at the hip, and have heard some of the stories before, but still are happy to hear them again.
“My podcast fans are the best audiences for my stand up. That’s where I always sort of announce dates first and really try to get as many ‘weirdos’ out to the show as possible. Because you know somebody might see Crashing and be curious and come out, but they might not know you as a person. But a podcast fan really knows your voice and your past and your history and your preferences and all these things. So as much as I can get podcast fans to come out, the better.”
Pete Holmes newest special Dirty Clean is available on HBO. Be on the lookout for Part 2 of our conversation with Pete in January, where we talk to him about Crashing.