ROGER CLINTON (Deadbeat Brother of Former Pres. Bill Clinton)
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.
DANIEL BALDWIN (Deadbeat Brother of Alec, William and Stephen Baldwin)
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).