If Bill Clinton is the best-case scenario for what an Arkansas good ol' boy can become, then his half-brother Roger is the worst-case scenario (Actually, he's probably more like the regular-case scenario, since we're talking about Arkansas). Either way, you'd think that a yearlong stint in federal prison for dealing cocaine in 1984 would be enough to scare him straight. Surprisingly, you'd be dead wrong. Although he (presumably) stopped slinging the yayo, Roger moved on to conspiring with the Mafia. According to TIME, the family of a Gambino crime family soldier handed a $50,000 check to one of Roger's companies in 1999, just months after Roger sought leniency from the U.S. Parole Commission for the mobster, who was serving a 45-year sentence for heroin trafficking. That's probably just a coincidence, though.
Beset by drug abuse problems for years, Daniel is the least successful of the Baldwin brothers. Unless, of course, you consider running naked through the halls of New York's The Plaza hotel a success-he's very good at that. So good, in fact, that the police came to watch in 1998-and then arrested him for cocaine possession. A slew of other embarrassments followed, including a July 2006 arrest for running a red light and crashing into two parked cars in L.A. In Baldwin's defense, however, he was going a remarkable 45 miles over the speed limit, which is technically pretty awesome. And, while Daniel has further shamed his three brothers by no-showing the season finale of Celebrity Fit Club and appearing in DVD-taint like 2004's Vegas Vampires, he redeemed himself somewhat by appearing on The Sopranos (although it was basically a joke at his expense).
The man largely responsible for creating the lovely genital-flashing young firecrotch we know today served a four-year federal prison sentence for stock fraud when Lindsay was just 11. Apparently, he missed prison life-he returned in 2005 for a slew of ridiculous crimes, including attacking his brother-in-law with a shoe and ramming his car into a telephone pole whilst shit-sauced. There are also reports of other violent episodes, such as punching a New York City garbage man for blocking his car (You have to admit, that one's pretty sweet.). Now divorced and scrounging desperately for a share of his daughter's fortune, Michael Lohan can at least take solace in the fact that, hey, one time he totally knocked the shit out of some sanitation worker, and that's better than having a family that's not ashamed of you.
It's largely believed that Ike Turner has been married 14 times (seriously), and while it's a lock that he's punched most-if not all-of his wives in the mouth for being uppity, Tina Turner is the most famous punchee. It's one thing to have a deadbeat relative who just embarrasses you before a performance (like Lindsay Lohan, for example), but it's quite another to have a deadbeat relative who very literally knocks five teeth outcho' head right before show time. And in addition to that most deadbeatish of traits, Ike's also lived through drug abuse, prison time, gambling problems and some questionable car crashes. Still, his most notable low-life move is derailing the talented-although very, very annoying-Tina's career/face.
Much like his Uncle Robert's brother Ted, Michael Skakel killed an innocent young girl after a night of partying. But very unlike Ted, Skakel took said life on purpose, bludgeoning Martha Moxley to death with a six iron in 1975. This fat son of a bitch's relation to the Kennedy family helped him evade prosecution until 2002, when he was finally convicted of the crime. One of the most disturbing moments in the Skakel story-and the only genuinely funny one-came in 1991 when DNA testing became available to investigators. In a pathetic effort to explain possible traces of his DNA, Skakel claimed that he had been masturbating in a tree outside Martha's home on the night of the murder. You know, just normal guy stuff. Everybody masturbates in trees at night, right?