From the minute they finished writing “Drillbit Taylor,” Seth Rogen, Kristofor Brown and Judd Apatow all began thinking of one actor for the title character: Owen Wilson, the accomplished screenwriter turned popular actor, whose work has ranged from Oscar®-winning films to blockbuster comedies. Wilson’s unique ability to evince both unhinged hilarity and moving vulnerability in the same breath made him perfect for the role of the homeless – or, as he puts it, “home free” – vagrant who plans to shaft the high school boys who want to hire him as their military-trained protector…until he begins to enjoy his new big brother position.
“We were excited to come up with a character for Owen doing the kind of comedy we’d always wanted to see him do, especially interacting with kids in a big, sweet movie,” says Apatow. “We are all such giant fans of his.” excited to come up with a character for Owen doing the kind of comedy we’d always wanted to see him do, especially interacting with kids in a big, sweet movie,” says Apatow.
Says director Brill: “Owen brought tons to this role, because he brings his own distinctive personality and his own Academy Award® nomination as screenwriter (for “The Royal Tennenbaums,” co-written with Wes Anderson). He was always punching up the dialogue, and throughout there was a great collaboration between Owen and myself, Kris, Seth and Judd. Every day was a blast. Owen plays Drillbit in a way that you’re always wondering if he’s a good person or a scumbag – there’s all this mystery and ambiguity and contradiction about him – but also he does it all with a smile and his own kind of comic edge. His Drillbit is sort of a philosopher/poet/madman.”
Early on, Rogen, who was then starring with Wilson in “You, Me and Dupree,” gave Wilson the screenplay and was thrilled that he responded enthusiastically. “One thing I realized on ‘You, Me and Dupree’ is that Owen is really hilarious with kids. He was great for this role because he can be dangerous-seeming and at the same time has that childlike quality,” says Rogen.
Adds Brown: “Owen is a great comic performer with wonderful spur-ofthe- moment instincts, but he also brings a writer’s sensibility to his performances. He came in everyday with ideas for this character that really helped bring him to life.”
Yet, it wasn’t just high humor that Wilson brought – it was also a raw humanity that gave the character a hint of poignancy behind his absurdity. “What surprised me is the depth he brought out of Drillbit’s character,” comments Brill. “We would do just completely dramatic takes of Owen tapping into being a homeless person and his real situation and that brought out some very interesting things.”
Years ago, Apatow had cast Wilson for his first major Hollywood role – as the hapless date who gets beaten up by Jim Carrey in “The Cable Guy.” “Judd, bless his heart, could see something there, a little diamond in the rough,” recalls Wilson. “And it’s kind of ironic that we’ve now made a movie in which I’m protecting these kids from the kinds of things that happened to me in ’The Cable Guy,’ such as getting my head dunked in a toilet.”
As with virtually everyone who read the script, Wilson could relate to the whole bullying situation that has put Ryan, Wade and Emmit’s high school careers in serious jeopardy. “I went to military school and everybody gets picked on in military school,” he notes. “You’re kind of getting screamed at and hazed and that’s just how it is. I also remember there was a kid in the neighborhood when I was growing up that we were all terrified of. Even more embarrassing, there was a girl who used to pick on us, that we were scared of because, when you’re only like 9 or 10, you don’t have a lot of strength. And this girl was, like, huge and she liked to fight. You know, there’s a lot about being a kid that’s kind of scary.”
Working with his teenage co-stars was also a revelation for Wilson. “I kinda felt intimidated because they were coming up with all this funny stuff,” he laughs. “Initially I thought ‘oh these poor kids are going to be so nervous on the set, but instead, they were just completely comfortable. Sometimes I wished they were a little more nervous.”
One of the unusually tough challenges for Wilson was playing opposite producer Apatow’s wife, Leslie Mann, as the teacher who falls for Drillbit Taylor, believing him to be the first decent, honest man she’s ever dated. “It seemed that Judd was always on set whenever Leslie and I had one of those passionate embracing scenes, so all I could say was ‘you know, it’s just a movie, Judd,’” Wilson laughs.
But the real fun of playing Drillbit Taylor was in the training sequences, when the character bluffs and blusters yet ultimately bonds with Troy, Wade and Emmit to build a friendship that transforms him into someone new. Wilson had a blast with Drillbit’s special techniques for stopping bullies, but notes it all comes down to one basic, very effective strategy: “His main technique is the ‘live to fight another day’ technique, which basically means just run away and stay out of the way of bullies – and really that’s a very valuable technique that applies to a lot of things in life. It’s really all about choosing your battles wisely.”
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