A flair for comedy

Four and a half years ago, Leslye Headland went on a blind date of the working variety with Jason Sudeikis, a man she knew only as “that goofy guy from Saturday Night Live.”

Each had been toiling on a project that would unleash a foulmouthed assault on gender politics: He as a star of Horrible Bosses, about three harassed workers plotting to murder their employers. She as the writer and director of Bachelorette, about an alpha girl who snaps when a high school bestie beats her to the altar.

Three hours later, “I was like, ‘Who is this guy?’” Headland recalled. “I’d never met somebody with such old-school Hollywood charisma. I felt like I was the only person he had ever talked to. And it was such a stimulating conversation, about everything from art to life.”

Inflamed by artistic passion, she composed a romantic comedy for him. “I was incredibly flattered to be viewed that way,” Sudeikis said. “And I was really moved by the story. I thought it was a great take on a genre that’s been both celebrated and beloved but also trashed and commodified. And on an archetype: the idea of whether, as the old song goes, lovers can be friends or vice versa.”

Sleeping With Other People propels Sudeikis into heartthrob territory after a career in which, wielding a smirk and a smart retort in films like Hall Pass and We’re the Millers, he’d become pigeonholed as what A O Scott of The New York Times called “a genial, excitable doofus who also happens to be catnip for the ladies.”

Headland padded that caricature with the most potent qualities of Sudeikis’ off-screen self-courtliness, a seductive intelligence — while mining her own romantic travails to write the role of Jake, a Columbia student who loses his virginity late, only to morph into a womaniser. Flash to the present, where Jake and Lainey — his partner in deflowering, now a serial cheater, played by Alison Brie — encounter each other at a 12-step meeting for sex addicts and go on a sort-of date. Fearing a backslide into old habits, they spend the rest of the film trying to subvert their lust. It’s unabashedly romantic and deliriously raunchy, a bonbon for a hookup generation longing for deeper intimacy but searching for it in the wrong places.

“In a film that was meant to dig deep into what was wrong with the rom-com genre and update it, you needed a Jack Lemmon you wanted to” have sex with, Headland said, using saltier language. “It couldn’t just be Billy Crystal or Bill Pullman or someone who felt safe. You needed a dangerous guy who was also super, super lovely.”

“Jason,” she added, “is always going to have that glint in his eye no matter what you have him doing.”

There certainly is something about Sudeikis. He took his time settling into the conversation, the distance narrowing as he revealed himself: an affection for Kansas, where he grew up in Overland Park, a suburb of Kansas City, Missouri. An adolescence fueled by sports until he stumbled into a forensics class at Shawnee Mission West High School. A basketball scholarship to a community college and the eventual realisation that he loved improv more. A 1997 move to Chicago with a singular goal, to attend the Second City conservatory, which he did before joining its Las Vegas company and performing sketches by Steve Carell and Tina Fey until the producers gave him permission to write his own. “One of the most flattering things is that some of those scenes are now toured. You talk about romantic, I’m romantic about that,” he said.

Then, in 2003, came SNL — a show he’d initially resisted trying out for, because he felt his artistic inclinations hewed toward the Blue Man Group, and “because I had a philosophy that it made people unfunny,” he said. At the urging of an agent who also represented Sudeikis’ uncle George Wendt (Norm of Cheers), he sent a tape to SNL.

Sudeikis was hired as a writer — like winning a gold in the triple jump when you consider yourself a long jumper, he said — and battled to have his sketches on the air, while aching for a chance to perform. Then, in his third season, there he was, making a name for himself in memorable skits with Kristen Wiig and, later, parodying ESPN Classic announcers with Will Forte.

Forte said he and Sudeikis were a contrast in styles. “I’m a real overthinker, and he blazes in and has these amazing ideas, but for some reason we meshed well together,” said Forte. “He’s a giving performer and writer. He’s looking for jokes for you as much as jokes for himself.”

That Sudeikis turns 40 might partly explain his desire to take on more emotionally resonant characters. “My own human exposition definitely informs both the choice of roles and the way I go about attempting to execute them,” he said.

Coming roles include another romantic turn, this time opposite Rebecca Hall in Tumbledown, and the part of the coach to Olympic runner Jesse Owens in Race. Increasingly in projects, there’s a character he gravitates toward, someone he has often sought out in his life, he said, “someone who sees a little bit more in you than you know you have to give, because sometimes we can get in our own way.”