Kyle Kinane is pumped to try some pizza. It’s the middle of the afternoon on the Sunset Strip and he’s settled into a dimly lit booth inside the onetime den of sin known as the Rainbow Bar & Grill. For the unfamiliar, this was ground zero for hell-raising ‘80s glam rockers like Mötley Crüe and Guns N’ Roses, as well as the spot where Motörhead’s Lemmy Kilmister lived out much of his twilight years, posted up at the bar like a salty, living statue.

Kinane has clocked a good bit of time at the Rainbow since moving from Chicago to L.A. in 2003 to pursue stand-up comedy. Now, at 39, he’s settled into a comfortable groove as a successful stand-up, headlining festivals, serving as the voice of Comedy Central (yep, that’s him!), appearing in his own hour-longs and on scripted fare like the Netflix series Love, in which he plays Gillian Jacobs’ scuzzbag ex-boyfriend. That archetype—the underachieving everyman swilling Bud Light—is one Kinane has doubled down on to impressive results, though his crackling wit and skyrocketing career suggest an altogether different character.

On this sizzly fall day, Kinane digs into his first slice at the Rainbow and opens up about the political comedy, cherishing palm trees and his brand new, hour-long Comedy Central special, Loose in Chicago, which airs tomorrow.

What are the details on the hour-long special?
I recorded it in May and it’s called Loose in Chicago because I recorded it in Chicago, and it was pretty loose when I did it. I had overcooked the material a little bit. I’d been doing it for so long. I’d been ready to do it in the fall and then the recording date got pushed back. [pauses] Yeah, lemme say negative things about it. Let’s do that. No, I was engaged but I was just happy to get the material out. Also, because of that, I was a little bit more excited to dick around with it; have a little more fun. I wasn’t so scared to stray from the structure that I had.

That sounds kind of fun and freeing.
It’s freeing! I don’t know if anybody else likes it. Freeing for me and what people enjoy can be two different things.

How does this special differ from your others?
There’s a little bit more outward criticism on this instead of inward criticism. I mean, I never get political. It’s not my M.O. I’m not smart enough to get political. There are enough comedians that do it very well that I know they don’t need my hat thrown in the ring for that. And when it’s not done well, it’s just somebody responding to a news story. Like, if I can’t offer a solution to the thing I’m criticizing, then I don’t want to just criticize it, ‘cause it’s cheap to do that. I’m talking to a comedy audience that is either in Los Angeles, which is wildly liberal, or who came out to see me somewhere else in the world, so that’s the liberal pocket of town. I see other comedians that do that stuff and people are agreeing with them with applause and woos. They’re not laughing. There’s no jokes anymore. You’re just reaffirming a position in front of people who know where you stand already. What’s the challenge?

With your success, do you now feel that elder-statesman responsibility to encourage younger comedians?
Yeah, sometimes that’s what people need. There’s a lot of self-doubt in the world, myself included. Especially when it’s not math; when there’s no answer. These creative pursuits—I mean, I admire people with self-confidence and people who can go into situations like, “I got this.” I was the opposite. I was like, “I’m gonna really eat shit on this.” And then, if I didn’t, I’d be like, “Cool! Pleasant surprise!” I guess I didn’t realize how valuable some encouragement is, especially for people that are funny but don’t know how to address groups of strangers yet.

And it can be hard to figure out how to naturally succeed in that element, even if your instincts are on track.
Yeah. You want to do a good job and make the audience laugh. Well, when the audience is a bunch of other comics, especially at open mics, it’s intimidating. It’s a lot of straight white dudes, though happily I’m seeing it be more diverse now. It had to be brought to people’s attention, that, yeah this is a bro-y situation. The guys in that scene don’t notice it because they were the outcasts: “Yeah, but I got picked on in high school!” But you’re still not someone who is transgender or gay trying to do a show. Or, just a fucking woman trying to make a room full of dudes laugh. It’s a very intimidating process for everybody.

Do you see yourself ever leaving Los Angeles? Returning to your roots in Chicago? Or does this feel like where you are permanently?
Oh, I live here. In Chicago, in the wintertime you just wake up and it’s instantly miserable. The floor is cold and you look outside and your car is buried. Your day starts with you just going “Ahhh, fuck this.” I think it did a great job to forge a community, especially with comedy. So I appreciated it for that, but otherwise I was miserable—built-in antidepressants. As a Midwestern kid, if I saw a palm tree, that was a vacation. I love the smell of air-conditioned air in a hotel. I know it’s trash, but that meant I was on vacation. That meant I was in Tampa, Florida, in a hotel with my parents and there was going to be a beach and swimming and drinks with pineapples in them. Still with palm trees, I’m like [pointing] “Gah! Look at it!” With movies as a kid I’d see a high school where their lockers were outside and say, “How can they do that? It doesn’t rain? It’s just outside? They don’t rust?”

You’ve been pursuing comedy for some time now. What are the ways you’ve seen it change?
Comedy is cool now. It’s a hip thing to do. You see so many people just jumping in, like, “Oh, I can just be really wry about my observations?” and it’s like, fucking NO. Write jokes. You need to write jokes. “That’s my whole thing is that I don’t write jokes.” Fuck you, write jokes. Learn that, then learn how to not do that. You can’t deconstruct something unless you know how to construct it first. So it definitely has a lot of dabblers now. Because I don’t think people are scared of it anymore. Now everybody knows a comedian. It’s not this embarrassing secret you have to have, like “I’ve been doing open-mic comedy.” People are like, “I’m gonna hit this open mic!” People aren’t ashamed of it anymore. I miss that a little bit. I miss when it was a shameful pursuit.