1. Soon-Yi Previn And Woody Allen
And their age difference isn’t even the creepiest thing about them.
2. Calista Flockhart And Harrison Ford
Who knew Kay Kyser was a person? That’s the greatest name for a musician ever.
3. Wendi Deng And Rupert Murdoch
Moral of this story? Rupert Murdoch is really, extremely old.
4. Ana Araújo And Ron Wood
Ron Wood has actually dipped into the much younger woman well multiple times. Ana’s actually older than his last girlfriend. So I guess that’s an improvement?
5. Jennifer Wade And John Cleese
Big band music. When John Cleese was a kid people still LOVED big band music. That is old.
6. Ashton Kutcher And Demi Moore
I have to be honest. This one wasn’t as dramatic as I’d assumed it would be.
7. Cortney Stodden And Doug Hutchison
Obviously, this one is the creepiest. The “Puffy Shirt” episode of Seinfeld debuted only two weeks after she was born. He on the other hand was born while Gunsmoke was king. Creepy.