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When Kyle Kinane first started to appear nationwide on comedy bills around six years ago, his life was in a very different place. He’d moved from Chicago to Los Angeles in the pursuit of a comedy career long ago, but he still held a full-time day job.

Since then, he’s become a fixture on Comedy Central both as the network’s voice for announcements and as a regular presence on shows like Drunk History and This Is Not Happening, but his on 2010 album Death of the Party, he explored his uncertainty about any future success. Death of the Party defined Kinane as a comic who could paint hilarious and complex scenes from his overactive imagination (like imagining the Trader Joe’s namesake as an actual person), but it was also an album wherein paying student loans, holding frustrating jobs, and dealing with insomnia were his primary concerns.

Kinane’s optimism shone through on even his darkest stories. This is a man who managed to turn a poop joke into a story about “the triumph of the human spirit,” and his good nature has remained a staple of his work. In fact, on the opening joke on his latest special, I Liked His Old Stuff Better, Kinane takes what could be an irritating event and turns it into a way to redefine the concept of miracles. He has put everything from suicide to bizarre interview opportunities under his microscope and has found the humor hidden within. He also chooses amusing track titles that clearly have nothing to do with the tracks’ material. There’s no indication that “God of Thunder” is about a weirdo Kinane saw on an airplane or that “This Track Is Not Called Straight Outta Compton” deals with a laundry mishap, but it gives a strong sense of the small things that obviously entertain him (and therefore, his fans).

Kinane has two sold out shows at U Street Music Hall tonight. Arts Desk caught up with him to talk about the appeal of performing in music venues, the weirdness of college shows, and the over-saturation of the podcast landscape.

The first time I saw you live was particularly memorable for me because at the end of the performance, somebody threw a shoe at you.

Oh, yeah! That was at that first Bentzen Ball. I remember that.

Well, that was in 2009, so at this point, that can’t be the most ridiculous thing that’s happened to you while you’ve been onstage. Do you have anything stranger that’s happened to you in the recent past?

It’s funny—-that never chalks up to being the weirdest thing because of how many all-ages shows and seeing these bands and seeing so much crazier stuff. He didn’t even throw it aggressively. It kind of just tumbled onto the stage. So, I think just from hanging around with drunks for most of my life, “Yeah, he’s taking a shoe off and throwing it at me! Yeah. Whatever. Typical Friday night.” But once in awhile, I mistakenly get booked on a college and those never go very well. I had the mascot come and sit on the stage because of how bad I was doing at a college.

Why do you think those don’t go well?

Because 18-year-olds don’t know what the world’s about and I don’t know what 18-year-olds are about. I thought I was young at heart, but then I go to a college and this is initiation weekend—-whatever the first weekend is—-and there’s like, bouncy houses and face painting. This is what toddlers get for their birthday. You’re paying five figures a year for this place to give you a piece of paper so your life can be planned out. I wouldn’t trust this institution with the money. First off, I’m getting some of your money. That doesn’t make sense. They’re not always bad, but I go in there with a grain of salt.

I noticed that your most recent special is at the 40 Watt in Athens and your show up here is at another club, U Street Music Hall. These are places that don’t usually cater to comedians. What did you find appealing about that?

It was just all feeing very formulaic, just the entire stand-up comedy career. And that just doesn’t make sense. I can’t believe I’ve made it this far that I’m allowed to tell jokes for a living—-why can’t I further dictate some of the standards of my life? There are some comedy clubs that are great but there’s others—-a lot of times, it’s just people that get free tickets and they’re like, “I enjoy comedy. Therefore, anything in this building labeled a comedy club, I should enjoy and if I don’t, it’s bad.” That’s such a shitty way to, first off, go through life. If it’s a music club, if people are going, they’re going to see that specific show. They know what they’re going to see. Hopefully, people are bringing friends or people that haven’t seen me before. I’ve still got to try to win over new people. But somebody on a random date night on a Friday walking out and I’m trying to tell a story that’s 12 minutes long and they’re not into it two minutes in. Oh fuck. What did you want? You wanted dick jokes? Sorry, you’re not getting dick jokes. So, that’s why. The energy is just different in music clubs.

And you played in bands for a couple of years. What got you to move from music to comedy?

The amount of time that I played in bands when that’s just all I did every weekend was to drive to all-ages shows and going to see bands every weekend. And it was just a matter of, you saw bands on MTV and went, “Well, I don’t know how you became a band.” Then I saw local bands and was like, “Oh you can do that. You can get together with other people of your same skill level and try and learn these things together.” Comedy was the same way. I saw comedy on TV and wondered, “how did you get to that level?” And if I go to a comedy club, I’m like, “It’s some guy talking about his wife and kids. I don’t have a wife and kids.” Isn’t there something else? How else do you do comedy if you don’t have a wife and kids? And I found open mic nights and was like, “Oh yeah, it’s the same thing.” And it wasn’t about trying to get famous or anything, it’s like, “Yeah. I just want to do good at this show in front of 25 people.” This is up my alley. This is how playing in bands worked. There’s 50 people here. I hope half of them at least tolerate us and don’t walk out of the room. Alright. Those are stakes I can operate within.

Did you find one to be harder than the other?

I only did music for, like, a handful of years. And once I was in a band with my friends, and that was a blast. Yeah, we’re going to hang out anyway, we might as well bang on some things and make some noise. When I tried to be in a band with people that were just acquaintances, that’s when I was like, “Yeah, this isn’t nearly as much fun.” This is just work. And comedy has never become that part. Comedy’s never become work. I’m still doing this like, “Oh, this is fun. I’m going to go up there and try to pull something out of my ass that might be funny.” It’s still interesting to me.

I know that on Death to the Party you talk about having insomnia. Is that still when most of your joke writing happens—-on nights when you can’t fall asleep?

That was coming around when I still had a day job, too. I may have thought that insomnia was that I just didn’t fall asleep until 3 or 4 in the morning and I have to be up at 7. Now that comedy worked out and I can sleep in, the insomnia’s not really there anymore. So, that’s a good thing. Now, once in awhile, I’ll come up with some weirdo thoughts in the middle of the night. But a lot of it’s just, I got to witness something and I was like, “There’s something. There’s a joke here.” But I’ll just write the idea down and walk around with it for a week and a half until the whole idea hits me. Like, I saw a guy that was tagging a building, spray painting, but the car that pulled over to let him out to do that had its hazards on. I don’t know what the joke is, yet, but that’s inherently funny to me, so…I’ll sit on that one for awhile to figure out what the angle is. You get a clue and then you have to figure out where the clue fits into everything else.

And it seems like you try to make a more cohesive storyline out of your jokes. Has that always been the case?

Yeah. It’s just that I can’t write a lot of jokes, but I can write one and beat the shit out of it. That’s kind of where people came up with this idea of, “Oh, you’re a storyteller.” No, I just don’t have a quantity of jokes. I have one that I have to just kick around for 10 minutes. So if it’s seeing a guy in a plane eating pancakes out of a bag, I don’t know if it’s a story so much as describing a situation over and over and over again. But I’ll take it. Storytelling sounds cool. I’ll take that label. It makes me sound profound. It makes me sound like an author. I’ll accept it.

You’re traveling and performing a lot. Do you still have opportunities to kick around new material or has that become harder to do since you’re getting paid for more gigs?

Yeah, but that’s one of the reasons that being in a music club’s a little bit different. I think there’s more leeway to watch somebody experiment than in a comedy club. It seems like the expectation at a comedy club is to see a complete act. So, in a music club, there’s more leeway to screw around, but that’s also why I’m trying to tour the way I’m doing now in music clubs. Sometimes you go out and back; you go to Cleveland for four days, you come back for two. You go to Milwaukee for three days, you come back for another three. Not only is that exhausting in its own right, but I write new stuff when I’m up here in L.A., because I can bomb because I’m on a free show at a Chinese restaurant. I still want to do well, but I’m going to try the new stuff there and if it doesn’t go OK, that’s alright. It’s my peers and everybody knows that you’ve got to try new stuff. This is where it kind of gets worked out. That’s why I kind of want to be in town in L.A. a little more often, so I can keep generating new material.

It seems like there’s been a recent trend of comedians with podcasts, but you’ve not jumped on board. Is that something you’ve ever thought of doing? Is it helpful for comics in any way?

Every comedian fashions themselves an entertaining person to be around, whether they are or not. You can be a great comic and a real drip as a human being. And vice versa. Think of how many people that are hilarious, fun people to be around but would never want to try and do stand-up. But I’ve said it before: I think you need the same checklist and waiting period to buy podcast equipment that you do to buy a handgun. Just everybody just jumped right out into the podcast scene. Just because you can, doesn’t mean you should. That’s my thing. I’ve thought about it only from the standpoint of friends with podcasts seeing more people coming out to the shows—-only if it feeds into the stand-up act. Only if it feeds into the live act. But I have to listen to myself talk every night already. I don’t need to double up on how much I’ve got to hear myself talk out of my ass.

And then it’s recorded for posterity!

Yeah. I did do one thing, and if it goes, it’d be fine, but I just want to talk about ghosts and UFOs with my friends because that interests me. I don’t want to get together and go, “Let’s talk about comedy!” I do that every goddamn day. I want to talk about Bigfoot. And if that’s the podcast, then sure. I don’t know why all these ghost hunter shows are always so serious. There should be fun Ghost Hunters. That’s my angle. I won’t say never. Something could be in the works, but I think it’s overrun.