10 of History’s Most Famous Black Sheep

Less than favorite sons (and daughters)

Charles Adams was the son of America’s first vice president, John Adams, America’s second president. While history has almost forgotten Charles in favor of his brother, John Quincy Adams, a check of the national archives notes that Charles was almost kicked out of Harvard for getting drunk and running naked through the campus with some of his buddies. “Later,” recalls Marcus Baram of ABC News, “he descended into alcoholism, losing thousands of dollars in shady land-speculation schemes. John Adams called him “a madman possessed by the devil,” notes Kathy Benjamin of the trivia website Wierdworm. “His father eventually disowned him, while his brother became President. Ouch.

Less than favorite sons (and daughters)

Al Gore III “is a guy most Americans first heard of when Big Al spoke about his son's childhood car accident and near-death experience during a speech to the Democratic National Convention in 1992,” observe the pundits at City Pages. “And Gore says he began writing Earth in the Balance in the hospital where his son was recovering. What does Mr. Global Warming get in return? A kid counteracting daddy's goody two-shoes rep by repeatedly getting arrested on drug charges – most recently after being clocked doing 100 mph in a Prius! Better living through chemistry seems to be behind him now: He last was seen briefly skittering across everyone's radar when he climbed into the wrestling ring as “Kid Blanco” for the sake of charity.”

Less than favorite sons (and daughters)

Billy Carter – Jimmy Carter might be a Nobel Piece Prize winner, the 39th president of the United States, and a spokesman for Habitat for Humanity, but some baby boomers remember him best as the brother of Billy Carter, a loudly burping redneck Georgia gas station owner who considered himself a “country philosopher,” Billy was prone to outrageous pronouncements and spectacular alcoholism. He launched his own line of brew, Billy Beer, declaring his intention to become “The Colonel Sanders of Beer,” remembers City Pages. “Other career highlights including drunkenly urinating on an airport tarmac in full view of the press corps.” “All this was innocent,” notes Benjamin at Wierdworm. “Billy didn’t really become a problem until his involvement in shady deals with Libya. When the press inquired why he, a man with no background in foreign trade would be interested in something like that he replied, ‘The only thing I can say is there is a hell of a lot more Arabians than there is Jews.’ The ensuing fallout forced him into rehab and his brother to publicly separate himself.”

Less than favorite sons (and daughters)

Edward, Duke of Windsor, abdicated the British throne to marry Wallis Simpson, an American divorcee. “While this has been cast as one of the greatest romances ever,” writes Benjamin, “it was actually a dysfunctional relationship where both partners cheated, drank themselves to oblivion, and collaborated with the Nazis. Seriously. The former Edward VIII and his wife even met Hitler at his holiday home. Hitler’s plan was to make Edward a puppet king after he invaded England.” The royal family was so embarrassed by the former king’s unabashed Nazi sympathies that they exiled him to the Caribbean for the whole of World War II.

Less than favorite sons (and daughters)

James Vincenzo Capone – How could anybody embarrass a major crime family? Prohibition-era Mafia godfather Al Capone was one of the most notorious gangsters of all time, taking advantage of Prohibition to increase his wealth and power in Chicago. However, his brother “Vince” ran away from home to join the circus, fought heroically in World War I, and eventually became a policeman in Nebraska. Vince spent Prohibition shutting down the very illegal alcohol productions that were making his brother rich and powerful. Vince became famous in the Midwest for his dedication to law enforcement. From his jail cell on Alcatraz, Al Capone was said to have been mortified.

Less than favorite sons (and daughters)

Pauline Bonaparte – The little sister of Napoleon, Emperor of France, loved opulence. She used her servants as footstools. Napoleon had a habit of installing his family members as puppet kings and queens of the countries he conquered, so once she sold a country she didn't want for several million francs. Her illicit love affairs were so numerous and so flaunted that Napoleon finally forced her to get married, hoping to stop the public embarrassment. “When that husband died, he found a new one for her,” writes Benjamin at Wierdworm. “Pauline was not put off. She had one of the most famous artists of the time do a sculpture" – topless. Napoleon was mortified.

Less than favorite sons (and daughters)

Too many Kennedys to list – The Kennedys have a special place in the hearts of all Americans. No other family has given so much – slain World War II hero Joe Kennedy Jr., assassinated President John F. Kennedy, murdered U.S. Attorney General Robert F. Kennedy – not to mention tragic John-John Kennedy Jr. However, no other family has seen so much scandal, either. Teddy Kennedy’s presidential ambitions were permanently thwarted in 1969 when he drove a car off of Chappaquidick Bridge on Martha's Vineyard. His female companion drowned while he dithered ... and deep-sixed his high political aspirations. His son Patrick Kennedy, a congressman from Rhode Island treated for cocaine abuse as a teen, crashed his Ford Mustang into a barricade on Capitol Hill, then claimed he was disoriented from prescription medications – although police said he smelled of alcohol. He then checked himself into a drug rehab clinic in Minnesota. Years earlier, he had been hanging out in a Florida bar with his cousin, William Kennedy Smith, who was charged that evening with raping a young woman. Now, shall we begin listing the alleged affairs with famous actresses? Why are the Kennedys so prone to scandal? “It's hard to tell,” said Noemie Emery, author of Great Expectations: The Troubled Lives of Political Families, “but it does seem that it crops up in some ways in almost every political family.” Even Ronald Reagan had a son who denounced him and another who told the press that not only was he a ballet dancer, but he was gay – not exactly the Reagan family image.

Less than favorite sons (and daughters)

Roger Clinton – “If you don't remember that Bill Clinton even had a brother, it's probably because the president wanted it that way,” observe the editors at City Pages. “While Bill Clinton was on his way to becoming the leader of the free world, his half-brother Roger was being sent to prison in 1985 for cocaine trafficking. Little seen during the Clinton presidency, Roger stirred controversy not long after his brother left office when congressional investigators found evidence that the daughter of a Gambino family crime boss paid Roger Clinton's company $50,000 in 1999, just months after Roger had lobbied for an early parole for the heroin-dealing mobster. He also sought presidential pardons for other criminals. In 2001, Roger himself was pardoned by his brother for his earlier drug conviction.” A month later he was arrested again for drunk driving.