The scion of one of America's most prominent political dynasties, he was almost kicked out of Harvard for getting drunk and running naked through the campus with some of his buddies.
Later, he descended into alcoholism, losing thousands of dollars in shady land-speculation schemes and was rejected by his father, who considered him morally deficient, "a Madman possessed of the Devil."
A Kennedy or a Rockefeller? A Gore or a Bush?
No, an Adams. Charles Adams, one of the sons of President John Adams, was the black sheep of his family, whose outrageous behavior and alcohol-fueled hijinks were a continual source of embarrassment to his parents and siblings.
Long before Al Gore III was arrested for marijuana possession and the Bush daughters were busted for underage drinking and a slew of Kennedys had made headlines for committing crimes, America's most important families were plagued by embarrassing relatives.
Of course, every family has a few bad apples, the source of hushed gossip behind closed doors. While political dynasties have always commanded attention, when one of their ranks stirs trouble, breaks the rules or falls down drunk, the incident becomes irresistible fodder. Famous black sheep are held to a different standard. Sometimes they can even do irreparable damage to the political fortunes of family members.
So far, the arrest of former Vice President Al Gore's son, Al Gore III, Wednesday morning for allegedly possessing marijuana and prescription drugs, doesn't seem to pose a threat to his father's potential political ambitions. The elder Gore has repeatedly claimed that he is not interested in running for president again. But his son's plight and his announcement that he is entering a rehabilitation program seem to be drawing sympathy from political pundits and observers.
Other families have not been as lucky, especially the Kennedy dynasty, several of whose members have seen their careers stunted due to their behavior. Most noteably Ted Kennedy's presidential ambitions were permanently thwarted in 1969 by the Chappaquidick scandal in which he drove a car off a bridge on Martha's Vineyard. His female companion drowned, and so did his highest political aspirations.
His son Patrick Kennedy, a congressman from Rhode Island, crashed his Ford Mustang into a barricade at Capitol Hill last year, claiming that he was disoriented from the prescription medications Ambien and Phenergan, although officers at the scene said that he smelled of alcohol. The younger Kennedy, who has acknowledged being treated for cocaine use as a teenager, later admitted himself into a drug rehab clinic in Minnesota. He had recently expressed interest in running for the Senate, but since the accident, Kennedy seems to have lowered his ambitions to simply getting re-elected.
And in the category of famous black sheep, it's hard to leave out William Kennedy Smith, Patrick's cousin. Both Patrick and his dad were hanging out with William at a bar in Palm Beach, Fla. in 1991, the night their relative allegedly raped a young woman. Kennedy Smith was later acquitted of all the charges against him.
Are political dynasties really more prone to having black sheep in their ranks?
"It's hard to tell, but it does seem that it crops up in some ways in almost every political family," said Noemie Emery, the author of "Great Expectations: The Troubled Lives of Political Families."