A few nights ago – just as he had on 138 previous Saturdays – Jason Sudeikis stood onstage at Studio 8H in Rockefeller Center and waved goodnight to the Saturday Night Live audience. The 36-year-old cast member had been in only one real sketch that night – logging a minute-long cameo as an employee at an Alaskan fish cannery, getting big laughs as the kind of arch, knowing straight man he's perfected in his nine years with the show. But it was a bittersweet night, nonetheless. Because as SNL's 37th season drew to a close, so did Sudeikis' contract – and the way things were looking, there was a real possibility he wouldn't be back.

"This is the first time I've had a contract end at Saturday Night Live," Sudeikis says, sitting down to lunch at a restaurant in Manhattan's West Village. "I'm kind of in the trees." Normally, he'd be at a script meeting right now, or maybe across town shooting a guest spot on 30 Rock. But with no work obligations, and his bombshell-actress girlfriend Olivia Wilde away in Maryland filming a movie, he's instead trying to figure out how to be unemployed for the first time in years. "It'll be. . . . Gosh, I don't know," he says. "We'll see."

Since he joined the cast full time in 2005, Sudeikis has become one of its most consistent players. A comedic Everyman, Sudeikis can carry a sketch by himself (Joe Biden), deliver a solid backup (the cop in the Scared Straight! parodies), or steal the scene without even uttering a line (his red-tracksuited dancer on fake talk show What Up With That?).

The Saturday Night Live season runs from September to May – Sudeikis likes to call it "the school year." For the past few years, he's filled his breaks with more and more work, like a kid who spends his summers running from tennis lessons to math camp. Chances are good that you saw him in at least one project last year, whether it was Hall Pass, as a henpecked husband masturbating to Styx in his Honda minivan, or Horrible Bosses, as a buttoned-down accountant plotting to murder Colin Farrell, or Eastbound & Down, as Danny McBride's coked-up, washed-out, fist-bumping pal. This summer, he snagged his biggest film role yet, alongside Will Ferrell and Zach Galifianakis in the political fartfest The Campaign.

Sudeikis says he loves doing movies, but he admits that shooting The Campaign during the SNL season was hard. "It sucks having to go away," he says. "You miss the camaraderie, the inside jokes. I'd never missed a read-through in nine years, and I had to miss one. That stinks." He says there's a lot about the show he'd be sad to leave: the stellar crew ("The fact that our hair and makeup people don't win Emmys every single year is baffling to me"), his friends in the cast. But there's also stuff he wouldn't miss, like the frustration of laboring over a sketch till six in the morning for three days straight, only to see it get cut in Saturday-evening dress. "It takes a lot out of you," he says of the SNL grind. "We start from scratch every week. If you allow yourself to enjoy only the product and not the process, I don't know if it's worth it. You could dump all your heart and soul into it and get nothing in return."

Like most people who've been at a job for nearly a decade, Sudeikis has mixed feelings about SNL. "It's an amazing job and a horrible job," he says. "You really do serve the show." But sitting in the booth with a half-empty beer, he definitely sounds like he's moving on. "It's just like playing in a community college," he says. "Everybody knows they're not going to be there forever. Even the coach wants to go to a D-I school." And every time the show comes up, he talks about it in the past tense.

Leaving SNL is always a risky proposition. Give up a steady, hallowed, 22-week-a-year gig in the greatest city in the world on the off chance that it might lead to some movie work? As Seth Meyers might say: Really? There are arguments to be made for either side. On the one hand, Belushi, Aykroyd, Murray, Murphy, Carvey, Myers, Sandler, Ferrell. On the other hand, Chris Kattan.

Still, no matter how much he may want to move on to the next level, leaving the show will be hard. "I've left places before," he says. "I left Second City, I've left schools, I've left relationships. This is very, very different." He says his mom can always tell how he feels about the show by looking at his face during the closing credits, a.k.a. "the goodnights" – and during the last goodnights, Sudeikis looked like he was wiping away tears. "Goodbyes are tough," he says.In person, Sudeikis gives off the air of a good-natured bro – like the cool slacker honors student, maybe, or the frat dude who also likes Arcade Fire. He loves Tater Tots and Buffalo wings and cheap draft beer. And dressed in his rumpled Foo Fighters T-shirt, he looks about as unfamous as you can be while still having hung out with the band. (He says that when he does get recognized, it's often mistakenly as The Hangover's Ed Helms.) He uses exclamations like "Well, gosh!" without irony and says that if he hadn't made it in show business, "I'd probably be back in Kansas, coaching basketball and teaching drama."

Growing up in the Kansas City suburb of Overland Park, Sudeikis never dreamed of being a TV star. He liked comedy well enough – Beverly Hills Cop, ¡Three Amigos! – but he wasn't a nerd about it, and he wasn'tcha really even that into SNL. To hear him tell it, he wasn't even the funniest member of the Sudeikis family. That would be his father, Dan, then a corporate headhunter and inveterate jokester. "He's really quick," Sudeikis says. "One time he met Joe Biden at a campaign event, and he said, 'I gotta tell ya, Senator – you do the best impression of my son I've ever seen.' " His mother, meanwhile, is famous in her own right, as a member of the American Society of Travel Agents' Travel Hall of Fame. "When someone comes up to me when I'm back home," says Sudeikis, "there's no way in hell I assume it's because of something I've done. It's usually more like, 'You're Dan and Kathy's son, right?' "

When he was young, Sudeikis' big thing was basketball. He was a Bulls fan because Chicago was nearby and Jordan was Jordan, but he loved the Lakers even more because they had Magic and "Showtime." Sudeikis was a point guard too, and copied Magic's showboating style – a lot of behind-the-back passes and trash talk, the opposite of his team-player approach onstage. Then again, he also led his team in assists.

Sudeikis knew he'd never be good enough to play for his beloved K.U. Jayhawks, even as a walk-on, but he figured he could maybe play Division II ball somewhere. Then one day in high school he happened upon a meeting of the speech and debate club and saw them playing improv games. He was immediately hooked and asked where he could sign up. Little did he know he'd basically just walked on at K.U. The Shawnee Mission West forensics team had been state champs for 10 of the previous 11 years, and Sudeikis quickly got a crash course in some of the things that would one day make him famous, like improv acting and comedic scriptwriting. A jock till the end, he liked the competitive aspect of forensics and the fact that you could letter in it. His senior year, he spent hours transcribing the famous courtroom scene from A Few Good Men. When he and a friend performed it at the state championships that year, their team took first.

After graduation, Sudeikis enrolled at a nearby community college on a basketball scholarship. But on weekends he'd make the 90-minute drive back to Kansas City to take improv classes at a place called ComedySportz. "I started getting more of a thrill from improv when I failed than from basketball when I played well," he says. "And if that's not an indicator, I don't know what is." When his basketball coach red-shirted him for bad grades two years later, he left school, moved back in with his parents, and organized an improv night at a local coffee shop. In 1997, he moved to Chicago and began performing at the famed improv school Second City, the SNL breeding ground where John Belushi, Gilda Radner, Dan Aykroyd, and Bill Murray all got their start, and then on to Las Vegas, where he had a job helping found Second City's new satellite show.

Sudeikis was supposed to stay in Vegas for six months, just long enough to get the show off the ground. He wound up staying almost three years. He loved it out there: He lived near the corner of Flamingo and Koval, where Tupac was shot, and dated Kay Cannon, a fellow cast member who'd later become his wife. (They divorced in 2010; she's now a writer on 30 Rock.) When he wasn't performing, Sudeikis would spend his days eating mushrooms or smoking pot and cruising around town on his little Vespa scooter. He also got really into the Blue Man Group, and started practicing drumming nonstop in the hope that he might join the cast. In fact, he went so far as to shave his head, which, he recalls, laughing, even his friends who were in the show didn't do. "I was just enamored with it," he says.

But before he could become a Blue Man, Sudeikis caught the eye of a manager in L.A., who got him a tryout on SNL. He flew to New York and auditioned at a comedy club, performing for an audience that included Lorne Michaels and then head writer Tina Fey. (Fey, another Second City alum, sent him an encouraging email, which she closed with, "See you when you get here, rock out with your cock out.") Sudeikis was hired first as a writer and continued for two years before being promoted to the cast. He celebrated with beers at Heartland Brewery and hitting golf balls at a driving range.

On SNL, Sudeikis specializes in playing the straight man, an earnest, sometimes befuddled foil to the zany antics of Fred Armisen or Kristen Wiig. "It's always been my favorite kind of character," he says. "A straight man, written correctly, allows for just as many laughs as the clown." His favorite sketches are the ones in which he basically gets to be Jason Sudeikis, reacting to the insanity that's going on around him. He says his trick is to kind of put himself in the audience's shoes, to look around the stage like, "What's going on here? Do you see what these people are doing?!" He says, "The whole goal is to make it look easy."

Although his characters – both on the show and in movies – have a tendency to be horndogs or buffoons, there's usually an underlying Midwestern goodness that keeps them grounded and relatable. The A-hole character he plays opposite Wiig is, at heart, a clueless dolt who loves his wife; even his devil is a dude you'd like to have a beer with.

Still, that doesn't mean Sudeikis can't go a little dark. The sketch he's proudest of is one you've probably never seen. It aired only once, in 2009, and it isn't widely available online because of licensing fees.

"I had just gone through a really bad breakup," he explains, "to the point that even delivering 10 dozen roses or riding up on a white horse and getting Axl Rose and Slash to sing on her doorstep would not have worked." He'd recently seen Say Anything, and he found himself identifying with "a heartfelt romantic who's going after the wrong girl," as well as feeling "really cynical about the grand gesture. I thought, 'This fucking kid is gonna take a boombox out and just push play, and that's gonna win her back?' " he laughs. "I don't think so."

So Sudeikis cooked up a sketch in which he got to play "the angry version of myself." It opens with that week's host, Joseph Gordon-Levitt, standing in his girlfriend's front yard in a trench coat, blasting Peter Gabriel's "In Your Eyes" to win her back. Then up walks Sudeikis, the curious next-door neighbor, taking out his recycling. "Hey, man, why are you pointing that boombox at my neighbor's house?" he asks, and when Gordon-Levitt as Dobler fills him in, Sudeikis proceeds to ruthlessly and hilariously dismantle the whole scene, and a generation's swoon moment along with it.

"I don't think the sketch went horribly well," Sudeikis says now. "Nobody talks about it, and you don't get to see it because of the Peter Gabriel song. But it was right at the heart of a lot of personal stuff. That's when pain gets channeled into this thing. That was an example of me having something to say."

It's happy hour now, and Sudeikis still doesn't have anything to do, so we make our way to a nearby bar. The bartender, a cute brunette in a tight black tank top who, up to that point, had been watching Dr. Phil alone, either recognizes him or is just feeling flirty because she starts making eyes at him before he's even had time to order his Lagunitas. "Where've you been?" she coos. "I've been sitting here all day."

"We didn't know!" Sudeikis plays along gamely. "Had we known . . ." "I'm kind of insulted," she cuts him off, then adds, "I'm just joking." "I know," he smiles. "I'm joking too."

Chalk it up to his down-home good looks or his funnyman charm, but Sudeikis is really a stealth ladies' man. For the past eight months, he's been dating Wilde, best known as the hot bisexual doctor on House and the hot bisexual bartender on The O.C. For six months before that, he dated Mad Men star January Jones – he was even suspected of being her baby daddy, though he's since been cleared – and he's also been linked variously to Jennifer Aniston, Scarlett Johansson, and Eva Mendes. Those last three are all tabloid inventions, but nevertheless, he seems to be, how to put this diplomatically . . . punching above his weight.

"I actually just learned that term recently," Sudeikis laughs.

Oh, really? In what context?

"Someone else said it about me."

Sudeikis brings this kind of likable self-effacement to most parts of his life. He knows his career hasn't caught fire quite yet; when he hosted the MTV Movie Awards last summer, he jokingly described Hall Pass as "the highest-grossing movie in America on February 26 from 1 to 4 pm." But now things seem to be picking up. This summer, he and Aniston will team up for a movie called We're the Millers, in which he plays a pot dealer who hires a prostitute to pose as his wife in order to smuggle 2,000 pounds of marijuana across the border. (And Aniston plays the prostitute? "Well," Sudeikis muses, "she might be a stripper.") He also has a bit part in an upcoming ensemble comedy called Movie 43, in which he plays a dickish-sounding Batman who cock-blocks Robin at a speed-dating event, which alone sounds worth $9.50.

Right now, he's looking forward to enjoying the little things, like the vacation to Jamaica he has planned or having friends over to drink Scotch and play board games without worrying about his segment on "Weekend Update." Heck, he might even get to play a little basketball. He and Wilde played the other day on some courts near his apartment, where they challenged a couple of kids to some two-on-two. "Oh, we won," Sudeikis says. "I shot really well – at one point, the kid said, 'You shot 75 percent!' " Sudeikis smiles and gives his own little Jordan shrug. "When it rains, it pours."