One of the most chilling quotes to emerge from the Charlie Sheen flame-out didn't come from Sheen himself. Rather, it came from Tom Arnold, a onetime substance abuser-turned Hollywood uber sponsor who reached out to Sheen and was rebuffed. Arnold's exchanges with a member of Sheen's entourage, Arnold told the New York Times, was especially frightening: "I went to a person close to him and said, ‘This guy is in serious trouble with serious drugs. We’ve got to help him.’ And this person flat-out told me to my face, ‘We make a lot of money from him. I can’t be part of it.’ That tells you everything you need to know.”

Many people--Sheen most of all--stand to lose money from Sheen's decline. But to a certain extent, the very reason Charlie Sheen may not be seeking the proper help, may not be getting better, is because there are hangers-on close to him who stand to benefit from that decline.

Sheen and his coterie of enablers with business plans aren't the only such instances. Entrepreneurial bad-advisors are a staple of celebrity, and we've rounded up several of the more noteworthy ones here. If fame is a kind of stock, these are its most famous short-sellers.

Mark Cuban is reportedly one of the latest of Sheen's "coterie of enablers." The Dallas Mavericks owner and HDNet head reportedly reached out to Sheen, seeing his recent spike in fame as an opportunity.

Paparazzi make celebrities famous. And a celebrity made this paparazzo famous, briefly. Spears dated Adnan Ghalib a few years back, until their relationship strained over his continuing to sell pictures of her.

Patrick Aufdenkamp first came on the scene during one of Lindsay Lohan's many flameouts. He's been by her side lots since. Whether he's mitigating an already dicey situation or egging it on while presumably getting paid by her for style advice is the subject of debate.

Howard K. Stern was Anna Nicole Smith's lawyer and lover. Stern managed to score prescription drugs for Smith, using false names, before her death by overdose in 2007. Two conspiracy felony charges were leveled against Stern; recently, a judge dismissed the charges.

Sandeep Kapoor, Anna Nicole Smith's doctor, was charged along with Stern.

Kato Kaelin rose to fame during the O.J. Simpson trial, in which he testified, somewhat incoherently, against his former friend. His O.J.-related fame led to several T.V. appearances.

He hardly got into this for the money. But Andrew Young, of the Jonathan Edwards campaign for president, helped cover for his boss, even claiming to be the actual father of Rielle Hunter's "love child." That cover didn't last. Oh well. Young got a book deal.

Was Dr. Conrad Murray's a name you had heard before Michael Jackson died? The fame he gained was only notoriety, but by coming aboard team Jackson during MJ's decline, Murray stood to gain a great deal. In fact, there is a whole sub-category of celebrity short-selling doctor/pushers, dating back to those who medicated Judy Garland.