On a Sunday in April 2006, Gary Harris pulled up to D'Angelo's large starter mansion outside Richmond, Virginia, in a limo. Harris, the A&R man who'd first signed D'Angelo in the early '90s and who had overseen his 1995 debut, Brown Sugar, was on a mission: to escort the singer to Eric Clapton's Crossroads Treatment Centre in Antigua.

As he walked into the spacious kitchen, Harris knew this wouldn't be easy. Spread across the kitchen table, marble countertops, shelves -- nearly every available flat surface -- were empty alcohol bottles of all conceivable varieties. "There was scotch, vodka, beer," Harris recalls. "While I was waiting for him, he emptied the contents out of the corners of three or four bottles to get a shot." D'Angelo himself was unshaven, about 40 pounds overweight, and hadn't packed. "He was trying to act like he didn't know I was coming that day," Harris says.

According to Harris, it took more than five hours to corral D'Angelo into the limo. Then the real journey began. Four days after hooking up with him, Harris had only gotten the then-32-year-old D'Angelo as far as Puerto Rico, delayed by missed flights, a forgotten passport, and the singer's insistence on emptying every hotel minibar he came across. After two days of trying to coax D'Angelo from his room at the Ritz-Carlton in San Juan, Harris threw up his hands.

"I told him he can do whatever he wants, but I'm getting on a plane," Harris says. "D'Angelo broke down and cried," and then agreed to go to Crossroads. The night he arrived, Harris says, "he called everyone he knew to send him a ticket to get him out of Antigua." D'Angelo wasn't in denial about his alcohol problem, Harris explains. "He just wasn't prepared to deal with it."

Six years earlier, a very different-looking D'Angelo stood on a small platform at a soundstage in New York City. His muscled frame was naked, save for a small gold crucifix on a chain, nestled in the valley between his pecs, and pajama bottoms hanging impossibly low on his chiseled hips, exposing the lower regions of a flat, V-shaped torso that pointed suggestively toward his crotch. The pj's would be invisible in the "Untitled (How Does It Feel?)" video being shot that day. In it, the camera opens tight on D'Angelo's head before drawing back slowly to reveal this once-chubby choirboy in all his sculpted glory. The effect is gloriously uncomfortable. As the camera sucks him in, it feels intimate and intrusive, revealing and voyeuristic.

"We made this video for women," says Paul Hunter, who directed "Untitled" along with D'Angelo's then-manager, Dominique Trenier. "The idea was, it would feel like he was one-on-one with whoever the woman was."

The video was actually the second made for D'Angelo's sophomore album, Voodoo. (The first, an artsy performance clip for "Left & Right," stirred little interest.) It was part of Trenier's strategy to shed the artist's Brown Sugar–era image as a doughy 21-year-old kid sitting behind a piano. Although D'Angelo had been working out intensely with trainer Mark Jenkins, he was anxious about the video.

"Initially, to him, it seemed completely bonkers," says Trenier, who managed D'Angelo from 1996 to 2005 and still considers him a close friend. "He didn't quite get what I was saying. He kept going, 'What do you mean, 'naked'?"