What happened to Dudley Heinsbergen?

The true story of Stephen Lea Sheppard ... after Wes Anderson, and after Freaks and Geeks
Saved by Hollywood
Grown-up geek: Sheppard’s career stalled just like most child actors, though in his case the trauma came before fame

Stephen Lea Sheppard wakes early most mornings. About 6 a.m. he cuts an orange, makes tea, and sits at his desk, which has five video game consoles and two large computer screens stacked on top of it. For five or six hours he’ll play games, write reviews or talk online, sometimes to Richard Clayton in Virginia, his best friend even though they’ve never met. Sometime after noon he’ll clean up, head outside and wait for the bus that will take him to his job as a dispatcher for a cable company in B.C.

Twelve years ago, Sheppard was the most authentic geek on television. As Harris Trinksy on the Judd Apatow-produced Freaks and Geeks, he developed a cult following for his deadpan delivery and hyper-realistic demeanour, not to mention the wispy moustache, the long hair, and the body that looked so uncomfortable to be in. A year later, he played Dudley Heinsbergen in Wes Anderson’s The Royal Tenenbaums. Acting alongside Bill Murray, he delivered some of the funniest lines in a very funny movie. And then he never acted again.

Freaks and Geeks and The Royal Tenenbaums were two of the most influential comedies of the last decade. They are also the only credits on Sheppard’s CV. After auditioning on and off for a few years, he stopped looking for parts. At 29, he lives alone in a one-room apartment in Surrey, B.C., that he can walk the length of in 10 steps. There are boxes of role-playing games stacked along its walls.

Sheppard isn’t bitter. Acting didn’t make him a star, but being on set remains among the most important things he’s ever done. It saved him, really, from what his life might otherwise have become. “I know how close I came to growing up into an absolutely miserable, maladjusted wreck,” he says. “I’m a much better human being for having done Freaks and Geeks.”

Sheppard was born in 1983 and he grew up in Gibsons, B.C., on the Sunshine Coast northwest of Vancouver. His father, Daniel Sheppard, was a tiler and a fiddle player and, according to Sheppard’s mother, Denise Olson, a pretty bad alcoholic. Sheppard was the first-born, a bright kid who always seemed older than his years. His parents called him Mr. Lea until he was about six, using the middle name that he goes by to this day.

When Sheppard was five, Olson found out she was expecting twins. It was a difficult pregnancy; she was confined to bed for much of it and tight quarters brought her closer to her son. “We were like best friends when I was pregnant,” she says. “We played all kinds of games on my quilt.” Sometimes they would cut boxes in half and Sheppard would make mountains of them. Other times he would make up stories or play with G.I. Joes. “He was sort of a loner, but both of his parents were loners, so I guess it was kind of normal,” she says.

After his sisters were born, things got harder. Olson was studying to be a midwife, and the twins were a handful. Daniel Sheppard continued to drink. “I was totally overwhelmed,” Olson says. “I didn’t have a lot of time for Lea.” At one point, she brought him to a birthday party on the wrong day. For an entire year Sheppard wore the same pair of gumboots when the family was short on cash.

Despite a loving, if distracted, family life, he struggled at school. From first grade to the eleventh, he felt as though he “was a barely tolerable presence.” Bullying is too “reductive” a term for what he went through, he believes. It makes it sound “like a child’s problem—something to just grow out of.”

Sheppard never really knew how to talk to people his own age. “I didn’t really have a brain-mouth filter,” he says. At school, he paid the price. In shop class, a student whipped him with a bundle of soldering wire. Other kids made him feel “worthless and undervalued.” By high school Sheppard was a geek in a very un-Hollywood way. He was the weird kid in the corner, reading a book and giving dirty looks to anyone who noticed him. “In my experience, most people paying attention to me were sizing me up for attack,” he says. “Anyone who wasn’t, I scared away without realizing it.”

Olson was so busy with the twins, she wasn’t aware of the hard time her son was having, and things might never have changed had his father not died. Though he got sober when his son was 13, Daniel Sheppard died of cancer two years later. Olson was still at school, outside of Vancouver, so she sent her kids to stay with different family friends.

“The family I was with, we were out in the boonies of the Sunshine Coast and we were all going stir crazy,” Sheppard says. “So one day the matriarch of the family said, ‘Hey, I saw this ad for this audition for this show called Freaks and Geeks and I thought it would be a great chance for us to go out and escape the house for a while, because, well, all my kids are freaks and geeks, and Lea so are you.’ ”

Sheppard only agreed to go after he was promised dinner in town. Even then he almost missed his chance. He was sitting in a corner, reading a book, when the show’s creator, Paul Feig, decided to do a last sweep of the waiting room. He’d already cast Seth Rogen that day. “I walk into this one room and it’s packed with kids, and I’m like, ‘Uh, forget it,’ and I walk out,” Feig said in a recent interview with The Onion’s A/V Club newspaper. “And I was like, ‘Wait a minute,’ and I walk back in. Something stuck in my head.”

That something was Sheppard. Feig gave him a speech to read. “He just did it in his inimitable way, just kind of tossing it off, and it was another moment of like, ‘Holy s–t, I don’t know what to do with this kid, but we got to put him in the show somehow.’ ” Feig and Apatow ended up creating the part of Harris—an older mentor to the show’s main cadre of geeks—for Sheppard. People who know him say the casting was eerie. “I don’t know how much the character was patterned on him,” says Clayton, his best friend. But “Harris basically is Lea Sheppard.”

Sheppard was soon flying back and forth to L.A., filming episodes. But when he first arrived, he was wary. His default was to assume anyone nice was setting him up for some kind of fall. That lasted about three hours on set. “Everyone was either very warm and accepting,” he says, “or busy enough that I could see they had bigger things to worry about than how to treat me badly.” It was a revelation for Sheppard. He felt valuable and wanted, as if playing a geek on television suddenly made him less of one in real life.

Freaks and Geeks only lasted 18 episodes, less than a full season, and Sheppard was only in 10, but the experience changed him. It “showed me how the people telling me I had nothing to contribute, that I was a burden who could be tolerated only with scorn and resentment, were liars,” he says. Once the show aired, the kids back home started treating him like less of a pariah. The show also got him his next part: Wes Anderson cast Sheppard in The Royal Tenenbaums based on his work as Harris.

But after Royal Tenenbaums, Sheppard’s luck ran dry. Other cast members from Freaks and Geeks—Rogen, James Franco, Jason Segel—have become A-list Hollywood stars. And Anderson’s most recent film just opened the Cannes Film Festival. But while Freaks and Geeks improved Sheppard’s life, he was still a bit of a recluse when it was over. He didn’t know how to talk to people, let alone sell himself as an actor. He got auditions, but mostly blew them. He acted in one commercial. Eventually the calls dried up.

As a result, Sheppard spent much of his twenties online, living in his mother’s house, though he eventually moved out and got a job. Today he is still a bit of a shut-in and spends a lot of time moderating gaming forums online. He’s never had a girlfriend. He’s had trouble finding good work. He’d like to write more—he does video game reviews for Vice magazine—and even act again, but he isn’t sure how to make either happen.

Still, for all that, Sheppard remains, if not happy exactly, then grateful for the chances he’s had. He’s still coping with the fallout from the bullying. He still has problems with new people and probably always will. But acting, especially in Freaks and Geeks, made things better. “It was the first time I was somewhere where I was treated with dignity and respect,” he says. “I walked away with a great deal of hope.” In that way, he’s the opposite of the child-actor stereotype. It’s the rare case of a young person shown the way to a happier, more normal life by Hollywood—not corrupted, in other words, but improved, by his brief glimpse of fame.