Pete Yorn
MTV, Winona, blackjack -- so far the shaggy-haired singer-songwriter has won at every fame he's played.

Pete Yorn admits it's a strange affliction, his instant, obsessive nostalgia. He's sure that just a couple weeks from now, he'll drive by this beachfront dive bar in Santa Monica and wistfully recall the two hours he and I spent in a booth here, talking about his love life and his new record, The Day I Forgot. Years ago, when he was in college at Syracuse, he'd go home to New Jersey and compulsively return to all the spots where he and his high-school girlfriend used to hang out. He knows that such advanced sentimentality can be embarrassing, even debilitating, but he can't help himself. "There's a fine line between being emotional and being sappy," he says, tugging on the hem of his Small Faces T-shirt. "And sometimes too much nostalgia can spiral down and turn really depressive."

It's oddly comforting that a gut like Yorn can make himself feel like crap thinking about the past. You see, his first 29 years seem to have been aggravatingly charmed. Born boy-band pretty, Yorn played drums in a series of Jersey cover acts before moving to L.A. in 1998 to entrench himself in the city's resurgent singer-songwriter scene; within two years he had a contract with Columbia Records. Then came the glowing critical response to his first record, musicforthemorningafter. Two of its songs, "Life on a Chain" and "For Nancy (Cos It Already Is)," even got played on the radio and MTV, despite a pop climate that tends to ignore tenderhearted guitar slingers over the age of 23.

No wonder people are so desperate to attribute Yorn's success to his connections: His brother Rick is a high-powered Hollywood manager who represents Leonardo DiCaprio and Cameron Diaz, among others, while their oldest brother, Kevin, is an entertainment lawyer whose clients include Heather Graham and Ellen DeGeneres. What else could account for his vertiginous rise? Can one guy really be that lucky?

"I wouldn't call it luck, but he is definitely blessed," Rick Yorn says. "If he just played the drums, he would be one of the best rock drummers out there. He is that good. I mean, how many people do you know who can hear a song once and then play it perfect on any instrument, and then also write great songs? He certainly has good luck with women, though. I probably shouldn't say that, but it's true."

Indeed, Yorn was the Colin Farrell of 2002, coupling up with Winona Ryder, Minnie Driver, and, if you believe the heated rumors, many more. All this without so much as putting on a decent shirt or even combing his hair. "I just had my biweekly hair washing," he says, running his fingers through the damp tendrils on the the back of his neck. "I get bad dandruff. I was like Ally Sheedy in The Breakfast Club a few minutes ago."

Slacker sex god, critics' darling, hit-maker: Can Yorn keep the streak going with his second record? The Day I Forgot is more private and introspective than musicforthemorningafter - more like musicfortwoandahalfweekslater, when you're sitting alone, contemplating your mistakes. Yet, at the same time, the first album's pop sheen has been replaced with a brittle toughness reminiscent of the heavy-metal parking lots of Yorn's youth. "This is more of a flat-out rock record," he says. "At least I think it is. The temptation on the second album is always to go big, and I tried to go the other way. I tried to keep it simple."

Of course, reading about your every move in the gossips tends to complicate things. Last March, one of our country's finer news-gathering forces ran a particularly salacious item about Yorn getting hot and heavy with Heather Graham. "I remember hanging out with my brother Kevin and we saw those lies in US Weekly," he says. "He's like, 'Who gives a shit? Relax. Fuck it. It's just lies. Fucking go bowling and get over it," I did think it was weird that some shit about me would help sell magazines. But I can't complain about the press. I think they've been really good to me."

So what budding starlet is he having his way with at the moment? "I'm not dating anyone," he says as he looks at the floor. "I've been kind of...I think I have met girls and stuff that I like, but I'm still alone. I know I've got to go back on tour soon, so I've been trying to keep it light."

Quite sensible, don't you think? Everything about Yorn, from his approach to entanglements to his choice of wheels, betrays a caution more befitting the tax accountant his father wanted him to be than the rock star he became. He drinks light beer, in moderation. At our lunch he ordered a cheeseburger, then ate only the patty, avoiding the carb-heavy bun. A couple months ago, when it came time to replace the truck he had been driving since he got to L.A., he dropped a load of cash on a huge, option-laden SUV - a Volvo, of course. "It gets 259 miles on a full tank and it's really safe," he notes, as if he expected me to cut him a break on his insurance premium. "The navigational system is pretty cool. I like to keep it on, even though I usually know where I'm going."

When pushed, Yorn admits one excess, one chink in his implacable sensible armor: He likes to play games. He faces off against strangers on Yahoo in gin and backgammon matches for more hours than he cares to admit. Lately, he's craved some real action and has made himself a regular fixture at the blackjack tables at the Mandalay Bay in Vegas. Naturally, he's had nothing but good luck. "O ;ole to gamble a lot," he says, looking a little unsure whether to be boastful or ashamed. "I probably do it a little bit more than I should. I have a new system and it has really been working for me. I've won a lot more than I've lost. I am just hoping that I can somehow keep it going."

Then Yorn looks around for a piece of wood to knock on. He settles on the wall, which is probably particleboard but will do for the moment. "Dude," he says in the dead-serious tone of a man confronting forces he cannot control, "I'm very superstitious."