Dana Giacchetto & His Celebrity Posse: 10 Big Names From a Star-Obsessed Rolodex

Jay Moloney: The tormented CAA agent, Giacchetto's pipeline to the fastest-rising young stars and execs in Hollywood, killed himself soon after Giacchetto gave him an executive job. "He wasn't an addict, he was manic depressive," says Giacchetto, "[and] the most loving, life-affirming spirit -- a risk taker with huge balls and an even bigger heart."

Leonardo DiCaprio: "The Wolf of Wall Street is hilarious," says Giacchetto. "Few people know him the way I do, and I thought it was the best movie he ever did. I love him. I always will."

Kurt Cobain: Giacchetto's one lasting achievement was parlaying Nirvana's success into a $20?million payday for its first label, Seattle's Sub Pop, still a hitmaker. When The Hollywood Reporter asked Cobain's widow, Courtney Love, whether Giacchetto is the idealist he sees himself to be, she replied, "No."

Tobey Maguire: The Ice Storm star lived sometimes at Giacchetto's SoHo loft, where he reveled with pals DiCaprio, Kevin Connolly, Jay Ferguson and Lukas Haas. Because Giacchetto had fraudulently moved funds into Maguire's account, the star subsequently paid $197,500 to the bankruptcy trustee for Giacchetto's firm, according to court documents.

Ben Affleck and Matt Damon: The Oscar-winning screenwriters of Good Will Hunting dumped their investments before Giacchetto was arrested, reportedly because they resented him using their names to drum up business (both declined to comment).

Alanis Morissette: The singer stuck by Giacchetto long after others abandoned him. Giacchetto felt that Morissette, then the top seller on Madonna's label Maverick, deserved a slice of equity in the label. But he failed to convince Madonna, who declined to comment. Morissette did not respond to a request for comment.

Phish: Giacchetto's biggest investors lost a reported $4.7?million, and recouped part of it by forcing the sale of Giacchetto's art collection, including a Calder, a Stella and a Condo.

Michael Ovitz: "I never thought of him as ruthless; I just thought of him as knowing how to convene power structures," says Giacchetto. "I never saw him do mean things. Never. Honest to God. And that whole gay mafia thing" -- Ovitz famously blamed his downfall on the influence of gay Hollywood figures -- "was ridiculous. Michael Ovitz was never homophobic. Ever."

Michael Stipe: Giacchetto says he met with an investment banker touting the Bowie Bonds concept. Bowie got $55 million upfront for forfeiting 10 years of royalties on songs recorded before 1990, and, Giacchetto says, a banker wanted Cassandra's clients to participate. Giacchetto says he never recommended the bonds to his clients, but did talk about it with Stipe. "Michael was like, 'I already have $50 million,' " says Giacchetto, who adds, "We had just finished the [1996] Warner deal, which was reportedly worth $80 million. They didn't need it."

Steve Stanulis: Giacchetto's former cop/stripper/bouncer, now an actor, is shopping his memoir, Sex and the Shield. "Dana is one of the most generous guys I ever met, but being associated with his bizarro world hurts me," says Stanulis. "I was up for a role in The Good Shepherd. Leo was going to [star in it, before the role went to Damon] with [Robert] De Niro directing. Suddenly the rug was pulled, supposedly because of my Dana affiliation. Leo swore to me he had nothing to do with it."