Rufus Wainwright

It was an entrance worthy of Oscar Wilde himself.

Two-and-a-half years ago, at the Los Angeles offices of his label DreamWorks, decadent dandy Rufus Wainwright came slinking in like a fox fresh out of the henhouse. In his chic Kenneth Coles, leather slacks and a rumpled dinner jacket he’d worn the night before, he collapsed into a meeting-room chair, brushed just-washed strands of shoulder-length shag out of his bloodshot eyes and croaked “Coffee!” to the nearest intern. “I need some coffee as soon as possible.” The New Yorker had been up all night at the post-Oscars Vanity Fair party, he hastily explained, squinting against the sunlight, and he’d finally crept back to his hotel room around eight a.m. And the list of celebrities with whom he’d hobnobbed was stunning: Sting, Eugene Levy, Joaquin Phoenix, Simon LeBon, Courtney Love, Patty Hearst, John Waters, Catherine O’Hara, and, of course, one of his best friends in the music biz, Melissa Auf Der Mar. He didn’t need java, I reckoned—his champagne-induced hangover called for some stiff hair of the dog.

But Wainwright—who was then just preparing to release his second set of fey piano-folk songs, the debauchery-themed Poses—was flying so high on his own hard-partying profile, he couldn’t return to ho-hum Earth. The chisel-cheekboned, muttonchop-whiskered son of legendary artists Loudon Wainwright III and Kate McGarrigle had—since his critically touted eponymous debut in ’98—somehow managed to become everyone’s pet party guest, a regular recipient of every A-list invitation imaginable. Wingdings he not only attended, but often closed down in a typically drunken and/or chemical-related stupor. He was fun, all the stars seemed to agree, because he dared to be obnoxious, dared to teeter on the brink, dared to be a Wildean train wreck. Should he derail? Bravo, they might applaud. All the more charming.

In the early years of hawking his craft, Wainwright said at the time, he’d show up at bars and—after quite a few cocktails—begin to croon his originals from the pub piano. It was shameless self-promotion, he admitted. “But there was something kind of endearing about it, too, because I was probably the one who was the most drunk. I was not afraid to have a good time, not afraid to be outrageous and say, ‘I’m gonna be a star!’ There was nothing at all very subtle about me.” And he just couldn’t help it, he concluded—once night fell in Manhattan, he was out on the town boozing, usually bouncing from drawing-room sambucas to supper-club cosmopolitans, then straight into nightspot standards like beer, whiskey and tequila. Then, like a vampire, home to the mystic crypt before sunup.

Wainwright’s hands trembled as he steadied his coffee, a full five months before the 9/11 tragedy would change the world. Was there really anything wrong with such a selfishly carnal existence? he wondered. Especially when it led to such striking collections as Poses, which noted “Cigarettes and Chocolate Milk” as a couple of his less deadly physical cravings. The singer’s answer would come soon, and in life-altering ways he wasn’t expecting.

Wainwright’s dad, Loudon, was famous for his ’72 novelty hit, “Dead Skunk.” His mom, Kate, was notorious as one-half of an eccentric folk act, the McGarrigle Sisters. But Junior—despite his delicately nasal singing voice and operatically grand keyboard melodies—was fast becoming known as a blinding Roman candle of a personality—a performer whose self-destructive behavior was bound to burn him out way before his time. The only remaining question: Exactly how much wick was left?

Cut to New York’s swank Soho Grand Hotel, a few weeks ago, a day before the summer blackout shut down the bustling metropolis. Right on time, in strolls Rufus Wainwright, and some differences are immediately apparent. Gone are the long hair and whiskers—he’s sporting a new Friends-short style and boyishly clean-shaven face. No suitcases sagging beneath his lids, either—in his suede sandals, flared jeans and skinny T-shirt, he’s bright-eyed, bushy-tailed, totally alive. No double espresso required. Grabbing a seat in the bar, he surveys a phalanx of liquor bottles, shakes his head and orders an iced tea instead. Soon he’s pawing through his messenger bag, looking for a shirt he might wear to that afternoon’s photo shoot—a vintage U.K.-sold McGarrigle Sisters tee, with his mom decked out as a toil ’n’ trouble witch. He cackles over it with his peculiar laugh, a rat-a-tat-tat report somewhere between Fran Drescher and Woody Woodpecker.