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."