Billy Eichner on His TV Personas, Off-Screen Style, and Why He Still Uses Dating Apps

He broke through in 2011 with his in-your-face interrogations on Billy on the Street, snagged a role on Parks and Recreation, and now stars on Difficult People. But though many of Billy Eichner’s characters are manic, his off-camera persona is downright refined.

We all know that actors are different from the characters they play on TV, but Billy Eichner makes it easy for viewers to get confused. In each of his two acclaimed shows, Billy on the Street (on truTV) and Difficult People (on Hulu), Eichner portrays a loud, gay, fast-talking, celebrity-obsessed New Yorker who goes by the name of Billy.

Although the real-life Eichner fits the same description, he’s not nearly as unhinged as his Billy on the Street persona, who bombards people on Manhattan sidewalks with questions about the differences between Kris Jenner and Geppetto. Nor is Eichner as bitter and delusional as the underemployed actor-comedian he plays on Difficult People. One other difference: Eichner dresses a lot better than his schlubby, hoodie-clad alter egos. A self-described former fat kid from Queens, Eichner now has two stylists on retainer—one on each coast—and is quickly learning the ins and outs of Hollywood fashion, including the hazards of wearing too much bronzer to the Emmys.

VIDEO: Billy Eichner and InStyle's Laura Brown Play Around in Our Fashion Closet

In Difficult People, you and the show’s creator, Julie Klausner, play younger, less-successful versions of yourselves. Until a few years ago you had trouble finding work even though you’d developed a loyal fan base of comedy and theater insiders. How are things different now?
Well, I always worked very hard, but now I’m finally getting paid for it. I remember my dad used to say to me, “If you’re such a genius, how come you can’t get three lines on Law & Order?” I told him, “Dad, show business doesn’t always make sense.”

Billy on the Street is now in its fifth season, and your celebrity guests include stars like Jon Hammand Lupita Nyong’o. A lot of people don’t realize how much effort goes intoeach episode despite its lo-fi look.
I think it’s the hardest thing I’ll ever have to do. There are so many variables because I’m out there on the New York streets and I’m screaming at people and improvising the entire time. The celebrity guests we’ve had on the show come in thinking, “Oh, this will be a fun, silly thing,” and they’re in shock at how exhausting it is. I’m surprised at how much I still think it’s funny—the concept of interrupting someone going about their day. That still makes me laugh.

The 2015 segment with Michelle Obama and Big Bird—in which FLOTUS pushed you around in a grocery cart after answering trivia questions about the 1980s sitcom The Facts of Life—was nominated for an Emmy. How did you get the First Lady on your show?
She approached us! I’m pretty shameless, but I would never in a million years have thought to pitch Michelle Obama. But the Obamas are incredibly media-savvy, and she wanted to promote her Eat Brighter! campaign and find the right creative partner to do a video. We shot it in a supermarket instead of on the street, but we wanted to keep things spontaneous and unscripted, so she didn’t know her questions in advance. She was lovely and got the absurdity of it. I was crazy nervous.

There’s a stereotype that all great comedians are, on some level, deeply tormented people. Are you?
No. I was a relatively happy kid with great parents. I wasn’t damaged, unless you consider my obsession with show business to be unhealthy. Maybe there’s a case to be made there. I was a fat, gay Jewish kid who sat around and watched a lot of TV and absorbed it all like a sponge.

You still draw upon that obsession in your work. Which shows are you addicted to?
The Comeback, with Lisa Kudrow, is my No. 1 show of all time. That got some bad reviews when it came out, and it taught me that sometimes the critics don’t understand. Oh, and The Wendy Williams Show is totally underrated. I love Wendy—always have, ever since she started out on radio. She doesn’t get enough respect. Who else is good at daytime talk shows anymore? Nobody! But there’s Wendy, pulling in viewers every day.

At what age did you start to care about your personal style?
I was always the nerdy performing-arts kid, but in my senior year of high school, I began to be aware of how I looked. I cut my hair and put some gel in it, which was a big thing for me. Subconsciously, I was probably thinking, “Oh, you’re going to want to start having sex in college, so you should look better.” I’ve always been very pragmatic.

Did you commit any fashion faux pas in the early days?
There were some talk-show interviews I did where I was dressing myself, and when I watched them later, I’d think, “Oh, no, no, no.” And the first time I went to the Emmys, the makeup artist was very heavy on the fake tanner—and I just let her do her thing because I figured she was the expert. Then I saw myself and thought, “That is not happening again.”

For your public appearances you’ve been wearing a lot of spiffy suits. These days some people might even call you dapper.
Right now I’m working a lot, and sometimes an industry party is my one fun event for that month. So you want to look good and enjoy it. Also, it’s important to show people the difference between me and my character on Billy on the Street. He has this low-rent jeans-and-T-shirt look, and I’ve realized that dressing better in real life helped people differentiate. So now I actually schedule the fittings in advance, because it takes hours. Hours! It’s shocking to me how long it takes, and I’m only trying on suits and ties.

You’re single, and you’re getting kind of famous. Is it hazardous to use dating apps?
No, I’m on Grindr and all that stuff—I just do my thing and don’t care. The younger generation, they take it for granted. At some point we’re going to have a president who was Snapchatting nude pics when he was in his 20s and nobody’s going to mind.

What about the perils of aging in Hollywood? When it comes to the pressures of staying young-looking and sexy, who has it harder, straight women or gay men?
Straight women, definitely. If you’re a woman in this business, you’re damned if you do and damned if you don’t. If you do get the surgery and it doesn’t heal in an ideal way, everyone says, “Why did she get all that work?” And if you don’t get it, they say, “She looks so old.” Or, “She looks great. What has she had done?” It’s really a no-win situation.

More and more men are starting to stress about it now.
Men might put that pressure on themselves, but I don’t think the industry is doing it to them. Maybe it’s an issue if you’re a certain type of actor. I imagine someone like Zac Efron feels pressure, but in comedy there isn’t quite the same standard, thank God. No matter what I looked like, Billy on the Street would have worked. So I don’t have that worry yet. Talk to me in 10 years.

For more stories like this pick up InStyle's January issue, on newsstands and available for digital download Dec. 9.

Photographed by Mona Kuhn; Styled by Jenny Ricker.