LONG, STRANGE TRIP

Bill Hader’s Journey From Playboy Call-In Sex Show to Romantic Lead

The Saturday Night Live alum opens up about his unlikely road to starring as a dreamy sports doctor opposite Amy Schumer in the hilarious comedy Trainwreck.

“I’m all right, maaiin.”

It was the summer of 2000, and Bill Hader was getting his first taste of Hollywood. A year prior, he’d dropped out of Scottsdale Community College and moved to Los Angeles to fulfill his dream of being a Hollywood filmmaker. Instead, he’d landed a job as a production assistant on the TV movie biopic James Dean tending to the wacky whims of its star, James Franco, who insisted on spending the entire shoot in-character. Hader was granted the unenviable task of fixing together PB&J sandwiches for Franco, who’d proceed to nosh on them, chain-smoke, and address the green, Oklahoman PA in his best James Dean voice. The following year, as a PA on Spider-Man, Hader was made to drop a hunk of concrete on Franco’s head during an explosion sequence. He couldn’t drop it right, and was chewed out by director Sam Raimi. Dealing with the enigmatic Mr. Franco, however, paled in comparison to his PA stint on Playboy’s Night Calls—a call-in sex show where Hader fielded NSFW phone requests from randy viewers, typically involving costumes they wanted the talent to wear while getting it on, and then relayed the fantasies to its hosts, porn star Juli Ashton and softcore siren Tiffany Granath.

I’m sure you’re aware of his E!-ready origin story, but if not, he was then plucked from obscurity by Will & Grace star Megan Mullaly, who caught his work with the L.A. comedy troupe “Animals From the Future,” and suggested him to comedy sage Lorne Michaels. He made his Saturday Night Live debut on October 1, 2005, winning the audience’s favor with outlandish characters like his flamboyantly gay NYC scenester Stefon and Herb Welch, an inept and irascible on-the-scene news reporter with a penchant for microphone mishaps. And now, some 10 years later, he’s become the summer blockbuster movie season’s unlikeliest star, appearing in two of its best films: as Fear in the brilliant Pixar animated feature Inside Out, and as Aaron Conners, a charming sports doctor who falls for a commitment-phobe booze-and-sex hound (Amy Schumer) in Trainwreck.

Mere hours before my chat with Hader, the Supreme Court came down with a 5-4 decision in favor of legalizing same-sex marriage, and the 37-year-old funnyman is thrilled.

“It’s beautiful,” gushed Hader. “I have a woman who works with me and my wife who is married to a woman and I showed [the ruling] to her, and she started crying. It was such a beautiful thing. And I read out Justice Kennedy’s statement in the kitchen today and thought, ‘Wow. This is so wonderful.’”

“Between Stefon and The Skeleton Twins I get a lot of gay support, which I’m so happy about,” he continued. “I have this new fan base—I’ve never said ‘fan base’ before, I swear!—and I love it. SO thrilled. I texted Stef and said, ‘We’re now legal in all 50,’ and he said, ‘We did it!’”

In Trainwreck, which is directed by Hader’s pal Judd Apatow and written by and starring Schumer, Conners is a star sports doc who’s interviewed for a profile by Amy. He soon falls for her, attempting to pull Amy out of her self-destructive cycle of vodka-drenched one-night stands. Unlike Hader’s other roles in the Apatow Comedy Film Factory—the second rowdy cop in Superbad, an assistant editor for the E! network in Knocked Up, the brother-in-law who spends the entire film on Skype in Forgetting Sarah Marshall—Conners is the film’s “straight guy” who reacts to the impulsively erratic Amy. He’s also the film’s romantic lead, a first for Hader. And, after seeing the first screening of the movie at this year’s SXSW, several female critics I spoke with were quite vocal about how “sexy” they considered Hader to be—a word you probably wouldn’t have associated with any of his other film roles.

“I guess it has to do with being the object of affection of a character they might relate to?” Hader says with a chuckle. “I don’t know! I had a lot of fun making it. I always liked actors that shifted and tried things. I didn’t go into it thinking, ‘I’m going to be a romantic lead!’ It was just a really great part.”

And the part came as a big surprise to Hader. A couple of years back, he got a call from his pal Apatow, who said, “Hey, I’m going to direct this movie that Amy Schumer wrote and she’s gonna star in, do you want to come in and read for it?” Hader had done plenty of Apatow films before, but this was “by far the best script,” since it was fully formed, unlike other Apatow projects that are a bit more suggestion-filled and leave room for improv. Given his pedigree, Hader thought he’d be reading for the role that eventually went to Mike Birbiglia—Amy’s sister’s goober of a husband.

“I showed up and got my sides—as a bad actor I didn’t go over my lines—and I went, ‘Oh, wow, this is for Aaron,’ and I read with Amy and it went OK,” recalled Hader. “But I got to meet Amy and I thought, ‘Well, that was fun.’”

Hader left, and then got a call from Apatow requesting he do a screen test in New York with Amy. They filmed two scenes in the flick—the one where they first meet in his office (and visible in the trailer), and another where they’re lying in bed together and she shrieks, “Can you not touch me?” It went well, and Hader knew he had palpable chemistry with Schumer. “It’s not hard to have a crush on Amy—she’s awesome,” he said.

“I remember Judd took us to dinner afterwards and just sat and watched Amy and I eat together and then he took pictures of us,” continued Hader. “We all went to the Girls Season 3 premiere party at the Museum of Natural History in New York and Judd walked around with a picture of me and Amy and asked everyone, ‘Would you buy these two as a couple?’ So, I was in this weird limbo of thinking, ‘I don’t know if I have a job or not!’ And then Amy and her sister Kim played a funny joke on me that night where I left and they had put all this silverware in my coat pockets. I thought, ‘Gosh, I’m getting along with these people so well, I really hope I get this.’”Two days later, Amy texted Hader with one word: “Yay!” Confused, he responded, “Yay what?” to which she texted back, “Oh no!” She’d accidentally leapfrogged Apatow and broken the news to him of his casting.

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In addition to palling around with LeBron James, who plays his best friend in the film, Hader had to partake in his very first onscreen sex scenes.

“Usually I’m the roommate walking in on the sex scenes who goes, ‘Whoa, hey, buddy, didn’t see ya there!’” he said with a laugh. “Or I’m driving. In No Way Out, I would be the driver going, ‘Hey, where am I dropping you… Oh! Sorry.’”So what was the experience like for him? “I felt weird for Amy, to be honest. My whole thing was making sure she was comfortable. In between takes I was always like, ‘Hey, are you comfortable? Was that super weird?’”

Fake lovemaking aside, Hader has charted an interesting path since retiring from SNL two years back. He’s flexed his dramatic chops, playing the best mate to James McAvoy in The Disappearance of Eleanor Rigby, and most notably, as the suicidal gay brother to Kristen Wiig’s character in the excellent tragicomedy The Skeleton Twins. Later this year, he’ll co-star in Rebecca Miller’s indie rom-com Maggie’s Plan, opposite Greta Gerwig, Julianne Moore, and Ethan Hawke, and just wrapped filming the Roald Dahl adaptation The BFG for none other than Steven Spielberg. Needless to say, he’s come a long way from his sex show days, let alone his SNL ones.

“When you come from SNL, people have a very clear view of what you should be,” said Hader. “It’s not that that’s bad, but I’ve always been interested in other things, and playing other parts. A lot of the people in my [SNL] cast were interested in other things and really flipped the script as far as what people think SNL stars should be.”