It’s a Tuesday afternoon in the middle of January, only four days until Jason Sudeikis will channel Kenny Rogers next to Gwyneth Paltrow in front of a studio audience and millions of devoted fans. Although he’ll soon head over to 30 Rockefeller Center to begin preparing sketches for that episode of Saturday Night Live, at this moment, the affable, 35-year-old comedian can’t get his mind off swag—and not for nothing. After spending a week with the show’s cast and crew in preparation for her hosting gig in December 2009, Taylor Swift gifted everyone with signed, scented candles. For her part, Scarlett Johansson gave the group matching blankets. Natalie Portman showed her gratitude with pizza. What token, Sudeikis wonders, will Paltrow select? “Maybe she’ll get us all GOOP subscriptions.”

For the past seven seasons, Sudeikis has introduced to the world, via NBC’s enduring, iconic sketch-comedy series, a sub-pantheon of boneheads, from his alpha A-hole opposite castmate Kristen Wiig, whose misadventures found the duo buying a Christmas tree from Jack Black and investigating a crime scene with Kevin Spacey), to his spot-on impersonations of Vice President Joe Biden, American Idol alumnus Taylor Hicks, and, yes, a certain leisure suit-wearing, “Islands in the Stream”-ing country legend.

Like so many of the inestimable talents who’ve roamed 30 Rock’s 17th-floor hallways before him, the time has come for Sudeikis to entertain the idea of a post-SNL career, which he will begin to do this month with Hall Pass, a movie about sanctioned cheating directed by the Farrelly brothers. But for every Tina Fey who goes on to conquer the silver screen, there’s a Cheri Oteri or a Chris Kattan, whose recent credits include supporting roles in the Jessica Simpson vehicle, Private Valentine: Blonde & Dangerous, and Hard Breakers, a sand-and-surf comedy co-starring Tia Carrere, respectively.

Sudeikis, dressed casually in a hoodie and jeans, isn’t sweating his odds. “I’m not overtly political, but it’s tough to think anything is at stake when I’m not, you know, fighting a war overseas,” he says from a two-top inside a Hungarian bakery in Greenpoint, Brooklyn, a few blocks from the studio where the accompanying photos were taken. “What’s really at stake here? Not much more than the opportunity to fly first class more often than coach.” He lets out a stentorian laugh, something the Kansas native does often, but it’s not totally clear if he’s joking. “Hall Pass is a great opportunity for me, and it’s funny to see myself on a giant poster with Owen Wilson, a hero of mine,” he says. “The only thing at stake here is the opportunity to do that again.”

Well, that’s not entirely true. Things have been spotty for Bobby and Peter Farrelly, who co-wrote and co-directed Hall Pass, since their one-two punch in the ’90s with Dumb and Dumber and There’s Something About Mary. They could use a hit, and Hall Pass has all the makings of an overnight classic in the vein of The Hangover. Rick (Wilson) and Fred (Sudeikis) are best friends. Their wives (played by Jenna Fischer and Christina Applegate) are also best friends. When their marriages grow stale after a few years, the men are granted a “hall pass,” one week of temporary vow amnesia without rules, responsibilities, or wives—their wives at least. Predictably, the bro-dyssey unfolds more like an episode of The Simpsons than As You Like It, as Rick and Fred run into all manner of roadblocks, including young temptresses, a homicidal barista, and one very drunk woman with a spastic colon and an unrelenting, unfortunate sneezing fit.

Despite its unabashed embrace of fart jokes and adolescent sexuality, the film also explores the sanctity of marriage in a post-Tiger Woods age. “I don’t think there are any hard and fast rules on love or marriage,” says the newly single Sudeikis, his tenor betraying a hint of wistfulness. “They are malleable, living, breathing ideas between two people or nine people—whatever floats your boat or your religion allows you to do,” he adds, admitting that he accepted the role, at least in part, because of the way it so earnestly marries heart and humor, a pairing characteristic of the Farrelly brothers’ canon. “I approached the story from a very personal place,” says Sudeikis, who ended his six-year marriage to 30 Rock writer and producer Kay Cannon last March during production on the film. “I believe in marriage, but I also realize that its sanctity is on trial these days, with the divorce rate being over 50%, with the glorification of cheating, and with the fight for gay marriage. When I was going through my divorce, I had been granted leniency, more or less, by a woman I wanted to date. I took her up on that—started dating other people simultaneously—and that did not go well. I wouldn’t do it again.”

It’s unclear whether Sudeikis is referring to Mad Men bombshell January Jones, whom he began dating publicly last summer until they broke it off earlier this year. (More recently, he was romantically linked to Scarlett Johansson, something both parties have denied.) Sudeikis inconsistently guards his privacy, not necessarily because he likes to kiss-and-tell, but because he can’t understand why anyone would care about, or take seriously, the details of his sex life. He took a crash course in diplomacy after appearing this past August on Lopez Tonight, where he gloated to the host that he had seen Jones naked. It was a goofy moment, endearing even, but Sudeikis’ recent reluctance to discuss personal matters, or even utter the words “January Jones,” is telling. (For her part, Jones responded in People, saying, “He’s never seen me naked, nor will he after those comments.”) The actor will concede that constant media attention—the speculation, the photographers—did make things “much more troubling for the woman I was dating,” but he’s just as quick to poke fun at the whole thing. “I took classes to learn how to improvise better,” he says, “but I didn’t take any to learn how to walk the streets without putting my finger near my nose. Besides, dudes don’t sell tabloids—well, maybe some of them do, but they look a lot better shirtless, and they’re signed on to play a vampire in the next 18 months.”

At some point in the next 18 months, Sudeikis will star, not as a vampire, but as a man who wants to kill his employer, in Horrible Bosses. In that film, he plays one of three cubicle-crazy friends (Charlie Day and Jason Bateman are the other two) plotting against their superiors: Colin Farrell, Kevin Spacey, and Jennifer Aniston. This is the second time Aniston and Sudeikis have worked together, following the release of last year’s The Bounty Hunter. Although he doesn’t say as much, it seems his experiences with the much-maligned tabloid target have helped prepare him for the glare of Hollywood’s spotlight. “It’s so shocking to me that anybody would ever say she’s sad,” Sudeikis says. “If anything, she’s a very joyful person. The thing about her story is that it strikes people on a mythological level. At the very least, Jen, Brad [Pitt], and Angelina [Jolie] have all become archetypes from a John Hughes movie: there’s the head cheerleader, the quarterback, and then the stunning girl who smoked and dated the college senior.” If we’re aiming for accuracy with the Jolie and Billy Bob Thornton allusion, didn’t she date the college senior’s dad? “Well, if precision is what we’re after, she dated his blood,” Sudeikis says, laughing. “But they’re all more complicated than that, aren’t they? Aren’t you? Aren’t I?”

Sudeikis’ phone convulses on the table between us. As he looks down, his eyes widen and he whispers to himself, “Holy shitballs!” It’s a text from Will Ferrell. “This is just so crazy, because I look up to Ferrell so much. He wrote, ‘Hey, fuckface. Just a quick hello to say happy New Year. I hope the movie with Owen kicks butt.’” Although Sudeikis collaborates with A-listers each week on SNL (in one sketch, he even put Zac Efron’s foot in his mouth), he still can’t quite wrap his head around being considered a peer to the likes of Ferrell, Fey, or Wilson. With a self-effacing smile, he says, “Most people don’t even know my name, and the one in every 20 times someone recognizes me, I have to explain to them that I’m not Ed Helms or John Krasinski. We should all do a show together—no one would be able to make sense of who was who!”

Although Sudeikis claims he has never been motivated by fame (“Creative autonomy in a house with a pool and a pool table is the goal,” he says), back when he was an unknown actor working in Chicago at famed comedy club Second City, he kept a journal in which he once wrote down, “I want to feel noticed.” Not necessarily by fans, however, or by journalists. “I remember being very vocal about not wanting to work on SNL during my early days at Second City,” he says, “but it was probably because I thought I never could, like, Oh, she’s so ugly—I would never be with her. But then she asks about you, and all of a sudden you’re interested.” To hear Sudeikis speak—about his love for SNL, or the group of people at 30 Rock (he has guest-starred over the years on 12 episodes as Floyd, Liz Lemon’s boyfriend), or the cast and crew of Hall Pass—it becomes evident that what he’s always wanted was the affirmation and respect of fellow writers and comedians.

What began as a game of hard-to-get has grown into a full-blown love affair, with the rush of live performance and with his SNL family. Even after seven seasons on the show, Sudeikis is still one of the last people to leave its notoriously uproarious weekly wrap parties. And he’s never alone. “Jon Hamm goes the distance,” he says. “Jim Carrey came to the after-after party last week, and the Black Keys were certainly there. Betty White went home early when she hosted, but she’s a pussy.” The one celebration Sudeikis won’t soon forget followed his first episode on the show. “I remember going to the after-party, going to the after-after-party, and then going home, lying in bed, and watching that night’s episode on TiVo,” he says. “It was about 7 in the morning, and I was so emotional.” You were probably just drunk, I tell him. “You’re wrong, man! I was high!”

Photography by Billy Kidd. Styling by Christopher Campbell.