Saturday night is a lot less spicy without Stefon, the fabulous “Weekend Update” club correspondent that turned actor Bill Hader into a comic star. But fear not. While Stefon has retired from Saturday Night Live to a “haunted diaper” in Chelsea, as Hader tells me in our recent chat, the funny-man flexes his impressive dramatic chops in The Skeleton Twins, playing Kristen Wiig’s twin, Milo, a struggling actor. 

Aaaand, he’s gay.

During our talk, Hader discussed his “license to be totally fabulous” as Milo, his regrettable transgender-centric SNL sketch, and the savory highlights of his A-list make-out roster. 

Your lip-syncing to Starship’s “Nothing’s Gonna Stop Us Now” in The Skeleton Twins would make everyone on RuPaul’s Drag Race so proud.

(Laughs) You have to get me on that show! That would just be the best.

How much drag did you and Kristen observe while training for the famed lip-syncing sequence?

I mean, we had to learn that song, and we had a lot of fun doing that, but we didn’t have a lot of time. There wasn’t a lot of time in the day to do it. It was definitely a quick “we gotta go; we have a lot more to shoot today” moment, so it’s cool it all came out so well.

So, what you’re saying is you already knew how to sissy that walk.

(Laughs) I knew... I mean, I’ve gone out with enough of my gay friends to know.

The finger in the ear during the money note – was that Mariah Carey-inspired?

No, no. It was just me messing around. So much of that stuff was me just trying to make Kristen laugh and just knowing her sense of humor and what will make her laugh. I thought that was something that would.

You’re a natural in that lady garb. 

Oh, thank you.

Before The Skeleton Twins, how experienced were you with cross-dressing?

Well, I had done some of it at Saturday Night Live, but not in my life. Not a lot of cross dressing in my life. 

Not yet. 

Not yet. Maybe I will now. I remember we did a senior sketch in high school where we made fun of a group of moms called the “Brown Bag Lunch.” They were these moms who put a lot of money into our high school, who would have these brown bag lunch things where they’d sit around and gossip about school – just a bunch of rich moms. We did a sketch at our homecoming and I played the main mom. We just recently watched that – my dad found it – and I’m essentially doing Stefon. I mean, it’s pretty crazy. I’m in high school! It’s pretty insane. But, I look goooood! My wife’s like, “Wow, you look great. You’re an attractive woman.”

There’s a scene in the film where you go to a gay bar only to find yourself there on “dyke night”. What’s been your real-life gay bar experience?

You know, I haven’t hung out that much in gay bars, but I don’t go to bars in general. I remember going to one with writers from SNL. There was a group of us and we went to a gay bar, because two of our writers were gay. It was fine. I had a good time. But I don’t really go out. I’m reeeeally boring. (Laughs)

You’re such a dad. 

I’m a total dad. I’m really boring. I stay at home and I read. Because I did Stefon people assume that I go to all these clubs and I get invited to a lot of those things, but nah.

And yet you live this exciting life onscreen. I mean, you’ve maybe made out with more men than I have… and, Bill, I’m actually gay.

(Laughs) I have my wife run up to me a lot of times and be like, “Don’t brush your teeth. Let me kiss you. This is the closest I’ll get to kissing James Franco,” or whoever it is I just made out with. I’ve made out with Paul Rudd so many times on SNL it’s insane! 

You made out with Ty Burrell during the shoot for The Skeleton Twins.

Yeah, but it didn’t make the cut. I’m gonna tell you right now, that was actually pretty hot. It was a hot scene.  

What does Paul Rudd taste like? 

Support Our Advertisers

He tastes like chicken, and James Franco tastes like cinnamon. 

You even got to fondle Paul’s man-aries.

Yeah, I touched his nipples.

Bill, this doesn’t sound like a very boring life to me.

Yeah, I know. It’s weird because we’ll be doing it and our wives are just watching the show in the green room like, “Hahaha. OK, guys.” 

Given your history of make-out sessions with men: If you could play spin the bottle with any group of guys, who would you invite to that party?

Paul, James, Ty... 

But they’ve already been to the party.

Yeah, they’re already part of the party, but I just know they’re all good kissers. I guess those guys, and then to mix it up, Danny McBride because I feel like I’d get the shit kicked out of me. 

SNL has been criticized for its portrayal of the gay community and some of its homoerotic cheap shots. Did you ever turn down a skit or were you ever hesitant to do a sketch because it might offend the gay community? As a comedian, how conscious are you of avoiding stereotypes whether on SNL or in The Skeleton Twins? 

In Skeleton Twins I honestly didn’t think about it. The thing I liked about the script was that Milo being gay wasn’t his problem. That wasn’t the big issue in his life. He had a lot of other issues, and he just happens to be gay, which I thought was really great. 

A journalist from another gay magazine said something that I liked – that I didn’t try to iron out his gayness. He’s flamboyant, but he’s drawn from people I know, people I’m friends with, people Craig (Johnson, the director) knows. I mean, that “dyke night” scene was me basically just mimicking Craig. (Laughs) When Craig went (to me), “You know, you sit down” – and I could tell it was something that had probably happened to him before – “and you look around and it’s fucking “dyke night”! You kind of go, ‘Where’s the boys at?’” So that is me impersonating Craig.

As far as SNL is concerned, Stefon was the same thing. His joke isn’t that he’s gay – the joke is that he’s just really bad at his life. And that he’s on a lot of drugs. I don’t know if I ever said no to anything, but I know the transgender community got really mad at a sketch I was in about estrogen – Estro-Maxxx, about a pill – which made total sense. But it happens, and the show takes responsibility for it. We have a ton of gay people who work on the show.

In retrospect, would you have passed on that skit had you known it would offend the transgender community? 

Yeah. I mean, I think the writers wouldn’t have written it. I don’t think anyone wrote it to hurt anybody’s feelings, but once that happened it was like, “Oh yeah. Point taken. Sorry.”

Actors who take LGBT roles often say you can’t really play gay, but you’re effortless as Milo.  What’s the trick? As a straight man, how do you transcend sexuality for a role? 

I didn’t think about it that way, to be completely honest. You just kind of do it and you find a part of you that’s this Venn diagram, where you overlay with the character. So, my relationship with Ty Burrell’s character: I just thought of high school romance, that’s what I thought of – a girl I dated in high school and how that made me feel. And it’s also just kind of hanging out with Ty. He’s a really funny, nice guy. Things like that – actual feelings of like, “What a great guy, he’s so nice” – play into it. You have to be very open. He’s giving you something and you have to give back, and you just play off each other. But I trusted Craig. I was just like, “I’m gonna try a bunch of stuff,” and Craig would tell me if it was too much. Usually his note was, “You can go a little further with it. You don’t have to be so subtle.”

And if a gay man is giving you permission to go gayer, you know you can. 

Yeah, exactly. He’s like, “I think you can be a little bitchy to (Kristen) now. Be a little flippant. I think he would be sassy with Kristen right here.” I remember when I was in drag and he was like, “You have complete license to be totally fabulous,” because (I was playing him) the opposite. I would try to sometimes play him in a way that was too subtle, and Craig was like, “Don’t worry about people saying it’s gonna be stereotypical – these are my friends.”

Because of your role as Stefon on SNL, how often are you pitched gay roles?

Actually, not that much, to be honest. Let me think. This might be the only one that I’ve been sent. It’s interesting. During the Q&A, after the first screening of the movie at Sundance, someone asked us about (the similarities between) Stefon and Milo and I went, “Oh, yeah!” Craig, who is gay, took the question because I didn’t know how to answer it. I went, “Uhhh.” The only thing those two guys have in common is that they’re gay, which is a good way of answering it. 

Would Stefon and Milo be friends?

Craig says no, and I think he has a better idea than I do. Craig was like, “Oh my god, no.” I think Stefon would freak Milo out. 

I think Stefon would freak a lot of people out. 

Yeah, you would be missing for a couple of weeks. If you went out with him, you’d have friends, parents, people pleading on the news, “Where’s our son?”

Where is Stefon these days? 

He’s on the corner of 23rd and 9th some place. Somewhere in Chelsea hanging out inside a haunted diaper.