Most Famous Films: Annie Hall (1977), Manhattan (1979), Hannah and Her Sisters (1986), Vicky Cristina Barcelona (2008), Midnight in Paris (2011)
Most Horrible Act: Marrying his adopted daughter

The heart wants what the heart wants. (We should also point out that Woody was never legally Soon-Yi Previn's adoptive father.) Still, the neurotic director has been in her life since she was around 10 years old, when he was shacked up with her adoptive mother, Mia Farrow. That relationship hit the rocks when Farrow caught Allen with nude photos (taken by him, no selfies) of her then 20-year-old daughter.

Yes, legally there was no foul play, but goddamn we're talking about some serious emotional damage. And even though they weren't related by blood, the situation can't help but feel grossly incestuous. And predatory as well—Allen was pushing 60 when (he claims) the relationship started. 

Fast forward to the present and Allen and Soon-Yi are married, with two adoptive, pre-teen daughters of their own. We can only imagine how the "How Did You Two Meet" conversation went.