Luke Wilson is not a gambling man, but if he were, he could bet on a winning streak this summer, when he appears in no fewer than four films -- starlet sequels Charlie's Angels: Full Throttle and Legally Blonde 2, Masked & Anonymous (about a mercurial musician, played by mercurial musician Bob Dylan) and Alex & Emma, a romantic comedy in which he assays his first "leading man" role opposite Kate Hudson.
"I have friends that will call me up and say, 'Hey, I went to the movies and saw a couple of your trailers. What's the story?' You get the feeling you're kind of annoying people by being out there so much. But what can I say? I'm trying to make a living," says the plainspoken Texan, who was an accomplished track athlete before the independent short film Bottle Rocket (1994) -- cowritten by brother Owen and director Wes Anderson -- hurtled him into Hollywood when Columbia Pictures produced the feature version in 1996.
Since that auspicious debut, Luke, 33, has worked steadily in such films as Homefries and Best Men with then-girlfriend Drew Barrymore, Anderson's Rushmore and The Royal Tenenbaums and mainstream comedies Angels, Blonde and Old School.
While the actor limits his wagers to "little skill things like golf or shooting baskets," the New York novelist he plays in Rob Reiner's Alex & Emma is hunted by loan sharks to whom he apparently has significant debt. In order to cash in on his book deal, pay them off and live to tell about it, Alex has to finish his long-abandoned manuscript -- about a love triangle that unfolds as a story within the story of the film. That's where Hudson comes in, as the sharp-witted stenographer who gives him a run for his money when he falls in love with her.
"I'm probably one of the worst people with numbers you've ever met," says Wilson of his betting abilities. "My brothers always kid that they think I'm counting cards in Vegas, but I'm just trying to add things up. The pit boss always does come by and check me out, though."
While Wilson, who also dated actress Gwyneth Paltrow, dismisses a personal romantic streak ("I like to think I can keep a pretty level head," he says), the actor was visibly moved by his experience meeting and working with the legendary Dylan on Masked & Anonymous.
"Incredible guy," Luke says, "always someone who I've looked up to and admired. I can't believe I got to work with him.
"From what I understand he never listens to an album once it's done. For me, I kind of like that idea. I don't know if I could do that kind of thing, never watch a movie I was in, even if I thought it was a good one. I had some good talks with him. I had a million questions I would have liked to asked him."
And the actor is clearly proud of the project, whose cast includes Jessica Lange, John Goodman, Jeff Bridges, Penelope Cruz, Angela Bassett, Bruce Dern, Ed Harris, Val Kilmer, Giovanni Ribisi, Cheech Marin, Mickey Rourke and Christian Slater.
"I like to say I'm not affected by what critics say -- though I think maybe it's hard not to be -- but that's definitely one of those moments when I couldn't really care less if people don't like it or not. I like it and I know other people who liked it. And it's just one of those things like hearing a song -- you're either affected by it or not. That was just one of the best experiences of my life. I'll never forget that."
The ingenuous Wilson is curious about exploring different kinds of roles, and less so about the fame quotient. "I don't think in those terms," he says about the leading man challenge. "That's one of those things that will really hurt me personally, if I label a character or think about what it might do if it were to do well. I just try to do a good job with it."
There is just something about Wilson's understated handsomeness and simple charm that makes his good guys so sympathetic, but what the actor really relishes are characters with a bit of an edge.
"I really loved that movie The Big Lebowski, and how Jeff Bridges's character can be a little bitter or just not interested in things," he says. "Like the kind of guy I'd like to hang around with -- not that he's easy to hang around with. I like those kinds of characters, because they're more real and can be more interesting."
The guys Wilson does hang around with, however, see it differently. "I have friends that say, 'Why don't you ever play a jerk, Luke? 'Cause that's what you are. You'd be a great jerk; you could just play yourself.' They're always kind of kidding me about that."