Cameron Douglas: Michael Douglas may have followed in the footsteps of his famous father, but his own son Cameron has seemed more interested in emulating Johnny Depp's character in Blow. In April he was sentenced to five years in the clink after getting busted for dealing meth and directing his girlfriend to smuggle him drugs in an electric toothbrush—and the judge gave his family a scolding for going too easy on the boy.
Cyrus Shepherd-Oppenheim: Cybil Shepherd's son probably won't be racking up any more miles on United after being arrested for allegedly stealing from his fellow passengers' carry-ons during a transcontinental flight last January.
Christian Brando: The Godfather's oldest son is most famous for shooting his pregnant half-sister's lover, whom he suspected of beating her. After he got out of jail, he was romantically linked to Robert Blake's wife before her murder, and sued by his wife and stepdaughter for physical and sexual abuse. Coulda been a contendah? Not so much.
Alex Paterson: New York governor David Paterson has been exploring expanding the state's casino operations in order to compete with neighboring New Jersey. His 15-year-old son, Alex, would appear to be an enthusiastic supporter of the plan: In January, cops hauled him in after catching him shooting dice and issued a juvenile report claiming that he was "loitering for the purposes of gambling," though both Alex and his dad have insisted that the game involved no real gambling or actual money.
Patti Davis: The rebel of the Reagan family found her father's Republican politics so repellant she refused to use his last name, using her mother's maiden name instead. She acted out by smoking pot, dating one of the Eagles, and most famously posing nude in Playboy in 1994. Can it be a coincidence that her father was diagnosed with Alzheimer's that same year?
Sean Stewart: Rod Stewart's pop classic "I Don't Want to Talk About It" takes on new meaning when it comes to his son Sean, who has made a career out of living off his dad's fame while complaining about him at the same time. His accomplishments include going to jail for allegedly attacking a married couple with a brick (he pled not guilty, and charges were later dismissed), appearing on a reality show called Sons of Hollywood with Aaron Spelling's son, going on Celebrity Rehab, and most recently, telling TV judge Jeanine Pirro that he couldn't pay his trainer $5,000 because his dad wouldn't give him the money.
Redmond O'Neal: It's bad enough that Redmond O'Neal got arrested with dad Ryan for meth possession. What's even worse is that he went back to jail for violating probation, and when mom Farrah Fawcett was dying of cancer, he was forced to visit her bedside in leg shackles. She may have been an Angel, but he definitely is not.
Charlie Sheen: Dad made Apocalypse Now; Charlie made Hot Shots. Dad starred in The West Wing; Charlie stars in Two and a Half Men. Need we say more?
Caroline Giuliani: Her dad may have been tough on crime as mayor of New York City, but that didn't stop her from apparently channelling her inner Winona Ryder: In August, she was taken into custody after allegedly being caught by a security camera taking the five-finger discount at an Upper East Side Sephora. (Her older brother, Andrew, has had some issues of his own.)
Maya Marcel-Keyes: At the 2004 Republican National Convention, politician Alan Keyes described Dick Cheney's daughter, a confirmed lesbian, as a "sexual hedonist." Unfortunately for him, his own daughter came out the next year—and unlike Mary Cheney, she's also a self-described anarchist with a fondness for facial piercings.
Jenna Bush Hager: Back in the early days of the Bush presidency, Jenna Bush's hijinks—falling down at frat parties and receiving citations for underage alcohol offenses—offered proof that the apple doesn't fall far from the tree. More recently, her fumbling, bumbling performances on the Today show have provided further proof that she is her father's daughter.
George W. Bush: Forget about "misunderestimated," "make the pie higher," and "is our children learning?" As Oliver Stone's biopic made abundantly clear, it was supposed to be Jeb all along.