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Pete Holmes on the High Plains Comedy Festival and Silver Linings

Pete Holmes is a comedian whose irrepressible spirit has endeared him to audiences nationwide. His last special, Nice Try, the Devil, aired last year on Comedy Central to widespread acclaim; we named it one of the best comedy specials of 2013. Until a couple of months ago, Holmes also hosted the Conan O'Brien-produced talk show The Pete Holmes Show on TBS; his podcast, You Made It Weird, continues to feature in-depth interviews. Holmes is In town this week to co-headline the locally produced High Plains Comedy Festival with his friends and early colleagues Kumail Nanjiani and T.J. Miller. Westword caught up with Holmes to discuss doing festivals with his friends, the silver linings in the aftermath of his show's cancellation, and Adam Cayton-Holland's ridiculous name.

See also: The ten best comedy events in Denver this August

Westword: When did you become aware of High Plains? What made you decide to do it this year?

Pete Holmes: Most comedians do festivals because their friends are doing them. And that's why I'm doing this festival. I love T.J., I love Kumail, I love the guys who are putting it together. It's Adam Clayton-Holland, right?

Yeah. There's no 'L' in there, but yeah, he's the comic who put it together.

Oh, what'd I say?

"Clayton" rather than "Cayton." It's such a common misprint he has a whole thing about it.

He should just change it to "Clayton." What a ridiculous name. But Adam is great, his group -- the whole Grawlix crew -- is great. Whenever I go through Denver, I always like to go and do their late show. They're good guys; I like what they're doing in Denver with the comedy scene. I like Colorado in general. So, friends, good shows in a good city with a good scene? That's gonna be a fun time.

It's interesting that you started out with T.J. and Kumail in Chicago. It's weird to think that like a decade ago in Chicago, you could could have gone to an open mic and watched each of you guys eat a bowl of cold dicks up there.

Eat a bowl of cold dicks, did you say?

Yeah, I said that.

Yeah, you could have watched us all do our best. I remember, I've never really seen T.J. eat shit, he's just such a talented improviser.

He's pretty unflappable.

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Yeah, I remember watching him back then and thinking, "I don't know what this guy's deal is." Back in those days, my nickname for him was "X-Factor." That's how I had him saved in my phone. I don't know what it is, but he has this thing where he's untouchable. Don't get me wrong; I've seen him have softer sets. Sometimes, the crowd wasn't there, but he did a good job. Kumail's changed a lot over the years. He used to be very quiet and more like Woody Allen when he started. You have to keep in mind that this was like 2001, so 9/11 had just happened and he's from Pakistan. So that was a little tense -- for years; it wasn't just the month of September. It was interesting watching Kumail negotiate with that as someone who doesn't really make a big deal out of his race, but still had to come up with some way to address that in a disarming way up top. So I think that was an interesting time. I've said many times that I'm just waiting for somebody to maybe write a book, not necessarily about Chicago, but just about that crop of comics. It's interesting that so many of us were coming up through Chicago.

There's even a subsequent generation of Chicago comics in L.A. now, like Cameron Esposito and Beth Stelling.

Yeah, I know, there's something about it. It's a little bit, I have to assume, like Denver, where it doesn't have that burden of industry. I mean, L.A. is a fun town, but I can count on one hand the truly great comics that started there -- just L.A. guys who never worked the road.

The road is a great equalizer.

To a certain extent. I think the road is tricky. You can't do it too much and you can't do it too little, but too little is better than too much.

You think? I mean, I guess I've seen a few old road dogs hiding out from having to write a new act by doing a bunch of road gigs.

Well, when I say that, I'm thinking of a guy like Demetri Martin -- who I think is fantastic -- he worked the road, but waited until he got established. By then he was touring. There's a difference between touring and working the road. Working the road is how you start becoming a product of your environment, when you start killing at some truck-stop bar. There's nothing with killing at a truck-stop bar, but when you learn that that's what an audience is, maybe a little drunk and not paying attention, you develop into a certain type of comedian, and in my experience, they don't tend to be the comedians that are groundbreaking or unique. Someone like Stephen Wright -- that is the type of comedian who comes from the Comedy Studio in Harvard Square. Meaning: the audiences are Harvard kids. Not exclusively, certainly not exclusively, I still play the Comedy Studio. But look out for your surroundings.

I can't say this enough, and if you include it in the article, that'd be great, but I think too many comedians get obsessed for one reason or another, with filing "comedian" on their tax returns. You'd be so much better off putting down "bartender" or "barista" or "unemployed," and living in Portland or Denver, or staying in Austin or Chicago. T.J. at the time, I think he was doing promotions for like Captain Morgan at some bar and Kumail was working an office job and I was a waiter at Bennigan's. We did the road once or twice a month, tops. Just to get a gauge, to see if you can build some chops while you're finding your voice.

People can get overripe in their scene, though; and it can become like a feedback loop. Everyone here knows how to crush in a room full of dudes with waxed mustaches, but if you just kill it at like a biker bar, maybe you're getting at something more universal rather than entertaining a bunch of people with degrees they don't use.

Yeah, I mean, kind of. Again, I would -- by a million times -- rather crush for the waxed mustaches. We can make fun of hipsters all we want, but those are the people with their finger on the pulse. They're setting the taste for popular books and films. So you don't want to have no road, you want to be able to adjust to an unfamiliar host and setting, know where the light is, and then learning to be a professional, show up on time and do your time -- which is a skill in and of itself. But I wouldn't kill at a biker bar. I mean, I could improv and maybe do some of my easier jokes. But the more I develop, the more I realize that I like performing for a certain type of world-view. I'm from Boston, and I'm still not comfortable going up in front of people that look like my parents -- guys that look like my father and his work buddies. I don't know what those guys find funny, but I'm guessing it's not what I find funny. Keep reading for more from Pete Holmes. There are those rare moments of transcendence, though, when a bunch of dudes like that do laugh at what you think is funny and you're just flooded with good will. Like "the differences between us don't matter!" Even though after the show they'll get back into their cars, and listen to completely different music than you'd listen to, and drive off into a life that looks nothing like yours.

I remember something that Eugene Mirman told me. I went up to him and said, "We're killing in the East Village, but what do we do when we go to like, South Carolina or whatever?" And he told me: "There's an East Village everywhere. There's a Denver in every state. Go to Portland, to Seattle, Vancouver, Austin, Boston, Montreal, Chicago. The places you don't want to go are like Rockford, Illinois. Those are the sort of places where I'd play a biker bar and decide "this isn't for me" and that's fine. I'm not going to host a screening of The Royal Tenenbaums here and I'm not going to do my act here. You don't want your act to be bulletproof. Jim Gaffigan told me, "There are some crowds that you don't want to kill for," and he's absolutely right. If it's fifty bachelorette parties on a late Friday night show, and you destroy, then take a good look at your act. When you book your hour, it's a theater full of attentive, intelligent people who aren't drunk. So learn how to kill for them. Don't just learn how to kill in a roadhouse. You're a comic, aren't you?

Yeah, I was going to say that choosing your audience is a luxury few of us have at the beginning. I'm only a few years in. At this point, I feel like more of a comedy intern. I don't file "comedian" on my taxes and any money I've made at it is more like a stipend than income.

But you do have that luxury. When I was coming up, I did the road and discovered it wasn't for me, and that was a valuable learning experience. But you can choose where you're writing your material, which mics to go up at; you can choose which scene to get involved in. If the people to your left and to your right are good comics, that is you controlling your audience a little bit. I'd rather have five people at a mic who'd be aware of me trying to hack a Zach Galifianakis joke than a room full of people who wouldn't even know if I'd done his entire act.

Yeah, that's an empty feeling: watching a really uninspired joke crush a room.

That's the thing! I used to have those little touchstones in my act, where if the crowd laughed too hard at this one thing, then I wouldn't like them anymore. Those have left over the years, but there really were those saved bits. Usually the stuff I wrote in the first two or three years. They're funny jokes, but you know that you're bringing them back out. Like an old joke about how at a port-a-potty, you don't take a shit, you abandon a shit. That one's good for somewhere like Bonnaroo, in the comedy tent, where you're performing for 2,000 people and 1,500 of them are on mushrooms. Sometimes, it's your job to kill. To your point, having a laugh like that in the chamber is my way of saying, "Shut the fuck up, I'm going to dominate this room right now." I got that from working the road.

It's frustrating in L.A. because there are so many actor types who can do fifteen minutes, but they've never worked a day, you know what I mean. So that's displeasing. Still, they've got a better shot at becoming writers or actors. So I'd rather be here and be in the running to have my own show than be bulletproof. We know the road dogs who always kill -- even the more famous onesm who stay up all night doing coke and fucking waitresses or groupies. That never appealed to me.

Yeah, I've met those guys who act like it never stopped being 1989.

It never stopped for them, man.

So, as far as being able to work in a lot of different types of rooms, did it take some adjustment to do your monologues for the Pete Holmes Show? The studio environment seems like it could be inorganic to have cameras moving around, and the audience further away than usual.

Well, we tried to have the audience pretty close. We did like a catwalk thing so I could be as close as possible to them. It is an adjustment; the ceilings are really high, which creates a feeling of distance between you and the audience. The cameras are around and everyone's a little bit nervous. I used to do warm-up after our warm-up to put them at ease. If they were really hot, it just felt like cheating. Your name's on everything and they're so excited to see you. To you, and by that I mean to me, I'm just some guy. I've been me my whole life, so it's not exciting for me to see me. I'm always around. But the waiting in line and the hype of it could feel like the deck was really stacked in your favor. Then on the days when the audience wasn't good, or the material wasn't as strong, the challenge was to act like it was going well, knowing that even though there were only 150 people in the studio, there are potentially 500,000 people watching at home and who knows how many online. So you had to pretend it was going well, even if it wasn't.

That's a tough skill to manage.

I do that in my standup, too. That's a great Hannibal Buress thing, he told me that when most comics bomb, they look down. He does the opposite, he puts his head up. We're trying to interpret the audience. We think we're good at it, and sometimes we are, but sometimes we're wrong. Sometimes they're just a little behind you, maybe just a little tired. Sometimes the guy before you had a similar joke. I see a lot of comics jump too quickly into that bombing place, where they're like "Fuck you guys" or "Fuck me, I'm not good." Sometimes, if you just don't get nervous, you slow down and don't get that flop sweat, they'll come around. Something I learned from T.J. is that there's a way to riff with yourself, to create opportunities and be honest and really funny. There's always a play. I think that's why it feels so bad to bomb, especially if the guy before you or the guy after you does really well. There's a nagging feeling of, "I know there was a combination to that safe, and I just didn't find it." Some people are just better at finding it that night. Their number came in. I've had nights where I was the one guy who got them, and then the next night I'm eating a bowl of cold dicks again. Keep reading for more from Pete Holmes.

So, have you found any silver linings in the aftermath of your show ending?

Well, the silver lining is that I'm not making a show that is really difficult to make. Doing a show four days a week is a lot of strain to put on yourself, and I don't have the hardest position. I mean that more for my staff than me. The silver lining there is that we were working so hard that some of our friendships started to suffer and I'm happy to report that we're back to being normal friends. I don't feel like their boss anymore. The other silver lining is that I get to go back to my first love, standup. Work on that new hour. People have remarked that I've been positive about it, but it's not baloney. We did eighty episodes of television that have proven me to our small sector of the industry. It's makes ticket sales better, it makes meetings go smoother and they're easier to get. It's a wonderful gift and a calling card. I don't even feel sad that the show is over; I just feel grateful for what we got to do. It's only silver lining; I don't even see the dark clouds anymore. It was disappointing when it went away, but that hasn't followed me.

It's all still there, too, available to people whenever. It doesn't have the shelf-life of other talk shows because you weren't really topical.

It's the only non-topical talk show that I'm aware of. You could watch any episode any day and it would always be relevant. We were kind of tackling pretty classic tropes and timeless themes.

So, have you renewed your focus on standup in the past few month?

To a certain extent. I've renewed my focus on touring. But it was all the same: On the show we wrote the jokes and I'd do the monologues; now I write my jokes and do them that night. There's a lot more freedom and refining in standup because you get to do it more than once. But in the end, it's all kind of the same. You're just a little boat in the stream of comedy. You have a talk show, you're just a little boat in the stream of comedy; you lose a talk show and you're still just a little boat in the stream of comedy. You're just trying to be in your flow. My life doesn't feel all that different. I don't have to get up at the same time every day and I don't see the same people every day, we don't tape three episodes of television a day. But it's still writing jokes and telling them. Maybe when actors lose their jobs they sit around eating Haagen-Daaz, but you can't take standup away from me. Even if no one wants to hire me or pay me to do standup, I can still go around and do shows. No matter what level you're at, it's one of those things that you realize they can't take from you.

As long as you can take it, yeah. If you can persevere with very limited encouragement.

Oh, yeah, you can definitely take it away from yourself.

Did you have to suspend working out your next hour while the show went on? Most of the monologue jokes are one-and-done, and you had a writing staff.

Yeah, but for the most part they were all my premises. Some of them came from the staff, I'm not trying to take anything away. For the most part though, it was me saying, "This is how I feel about this thing, let's write a monologue about it." I did maybe 40 percent of the hour I'd had worked out on the show in different ways. Now I've re-written a new 40 percent. So I'm in the situation where I have some jokes that maybe people -- I mean, you'd have to be a pretty die-hard fan -- but if you saw me do an hour right before the show started and an hour now, you'd probably recognize about 50 percent of the jokes. Just because they're good jokes. The best ones. I don't want to stop doing them yet because I like them and I haven't taped them anywhere. But I'm slowly moving new stuff in. Certainly in the next six months, we'll do a special and I'll record them, but for now, I love doing them and when I don't do them people ask me why not, you know what I mean?

Not being on video is pretty much the unwritten rule, right?

Yeah. If you saw me do it a year ago and you're coming again, chances are you won't mind hearing just the very best of those jokes in between all this new material I'm excited to do.

So before we wrap up, I wanted to add that You Made it Weird was a pretty helpful free comedy university for me and a lot of comics I know when we first started or were just thinking about starting.

Thanks, man, that's good to hear. It's funny, because a lot of people ask me if I have any comedy advice and it's like, "Yeah, three hours a week for the past few years." There's a lot of standup advice; I've repeated and repeated all the great advice I've heard over the years, and then guests come on and offer their own. Standup is a weird thing. T.J. and I talk about that a lot, about how when we started out there weren't any podcasts to listen to, so there was nowhere to hear Mike Birbiglia telling you the secrets of touring. I'm really excited to see what the new crop does with this new Internet, this like, second Internet that's showed up. I think that a lot of comics are going to get better faster and I hope it brings the community together even stronger.

Pete Holmes is headlining the High Plains finale showcase at 10 p.m. on Saturday, August 23 at the McNichols Building. Visit the High Plains Comedy Festival's official website for tickets and to see the fest's complete schedule.

Follow Byron Graham on twitter @ByronFG for more mildly amusing sequences of words.

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