When you’re doing risqué gay material, how do you stay truthful without alienating a heterosexual audience?
As a gay performer, you have to figure out how to express some honest representation of homosexuality that isn’t just about performing gayness for straight people. A lot of gay comics don’t show that honesty so much as they reinforce what straight people already think of us. Early on there were definitely people who said to me, “You’re too out there and you’re talking about things you shouldn’t talk about.” But it’s my life. You may not like it, but I’m always going to be open about who I am and tell the jokes that are funny and interesting to me.

I recently saw a Judy Gold comedy special from the ’90s when her stand-up act was still weirdly straight. Was there a time your act wasn’t gay?
No. Nothing on this planet creeps me out more than somebody who’s a practicing homo but closeted onstage. I don’t understand how you can take pleasure in the stuff you’re talking about when you can’t talk about your real life. For the astounding number of lesbian comedians in the ’80s and ’90s like Wanda Sykes and Carol Leifer who came out later, I realize there was frequently a process of them figuring out who they were. For guys, it’s just different. I can understand how actors don’t want to be too strongly identified with their sexuality so they can take on different roles and still have believable romantic chemistry with a woman, but there’s no such excuse for a comedian. If you’re a closeted comedian, you’re just a coward. There was a time I didn’t want to use the gay thing as a crutch, so every other set I would try to talk about other things in my life. The problem was that some audiences would laugh just at the simple fact that I was gay, so I realized I needed to be on top of and in control of that laugh.

How do you craft a gay joke that’s funny without being offensive?
You have to determine if the joke simply rests on the preposterousness of homosexuality — “two guys having sex is hilarious!” — or if it honestly looks at gay culture and how it relates to straight culture. Basically, don’t objectify people and don’t be an asshole. We shouldn’t make fun of an out gay person for being out and gay; we should respect that. It’s infinitely more successful to make fun of a closeted, possibly gay person who’s pretty fuckin’ gay.

Writing jokes for Chelsea must be easy since she somehow gets away with saying just about anything.
It’s interesting to write jokes in someone else’s voice, which means that sometimes I have to pitch a joke about my vagina. Chelsea is very aggressive in the way she talks, but she does want to respect other people’s experiences and the stuff that she doesn’t quite get. Sometimes she makes a joke and we have to point out, “Hey, I don’t know about that one,” and she gets it. She once made the best tranny joke that felt so fucking true, but we couldn’t use it on the show. I can’t even repeat it.