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.

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