The 11 Most Notorious Cradle Robbers

When rumors swirled yesterday that Mickey Rourke and his The Wrestler co-star, Evan Rachel Wood, got caught making out, we were pretty impressed. She’s 21, and he’s 52. The cradle had officially been robbed. But how Rourke would stack up when pitted against the greats? We decided to put together a comprehensive list of legendary cradle robbers to find out.

#11 – R. Kelly – 42

No list of cradle robbers would be complete without the 21st century’s most unapologetic sex freak. R. is the youngest cradle robber on our list, and also stands out as being the only one who might technically be considered a pedophile. In 1994, Kelly reportedly married his protege, Aaliyah (RIP), who was fifteen at the time. The two had been busy working on her debut album, fittingly titled Age Ain’t Nothing But a Number. Since the marriage was obviously illegal, it was annulled, and Kelly went on to marry a woman closer in age to himself… But as we all know, the story doesn’t end there. In 2002, while still married, Kelly was arrested for having sex with a minor, putting it on tape, peeing on her on tape, etc. Her age? A very young 14.

#10 – Donald Trump – 62

The name Trump is synonymous with many things: real estate, power, ‘you’re fired’, ridiculous hair, and most importantly, ladies. From Marla to Ivana, Trump loves gorgeous women. His current wife is model Melania Trump (formerly Melania Knavs) who Donald has a respectable 24 years on.

#9 – Larry King – 75

Once a titan of radio and TV news, Larry is now a breathing corpse, famous for nothing more than wearing wacky suspenders and being a serial marrier. Larry has been married seven different times to six different women. The current Mrs. King is Shawn Southwick, a relatively unknown actress who is 25 years younger than Larry.

#8 – Jack Nicholson – 71

Jack is one of Hollywood’s most legendary sex fiends of all time. Maxim named him one of the ten living legends of sex, and he’s had relationships with everyone from Kim Bassinger to Angelica Houston to Candice Bergen. His most recent high-profile fling was with Lara Flynn Boyle, who he had 33 years on, and was substantially younger than two of his five children.

#7 – Clint Eastwood – 78

Clint is the second-oldest on our list. That means that even if he was married to a woman in her 50s, it would still be loosely considered cradle robbing. But Clint doesn’t do ‘loosely’. After all, this is Dirty Harry we’re talking about. So when it came time for Clint to take his current wife, he went big. None of that twenty-something bullsh*t. The current Mrs. Eastwood is Dina Ruiz, someone we’ve never heard of, but still, a healthy 35 years younger than Clint.

#6 – Billy Joel – 59

As he’s gotten on in years, the Piano Man has let his weight and facial hair get slightly out of control. For normal men, that’s usually a recipe for babe repellent, but for a hit-maker like Joel, it’s apparently catnip. After ending his high-profile marriage to supermodel Christy Brinkley in 1994, Joel successfully wooed and wed Katie Lee, a 27-year-old TV chef. Not only is that a 32 year age gap, but it’s also only five years older than Billy’s daughter!

#5 – James Woods – 61

Having only been wed twice, by Hollywood standards James isn’t exactly the marrying type. But while he may not rush to the altar, he can rob cradles with the best of them. He’s currently dating Ashley Madison, a 23-year-old wannabe actress. Previous flames have included Heather Graham, who he had 22 years on, and 28-year-old actress Alexis Thorpe.

#4 – Joan Collins – 75

Demi Moore is usually the only name that comes to mind when thinking about female cradle robbers. After all, she is married to Ashton Kutcher, a guy who is 16 years her junior. But compared to the men on this list, a 16 year age difference is peanuts. No, if you want to throw a lady on this list, it has to be actress Joan Collins. Joan has been married five times in her 75 years, and her most recent spouse is Percy Gibson, a man who is 32 years her junior. Now that’s giving the guys on this list a run for their money!

#3 – Hugh Hefner – 82

Calling Hef a cradle robber is slightly unfair. Yes, the man dates girls who are waaaaay younger than him, most recently 23-year-old Kendra Wilkinson (that’s almost a 60 year difference!). But when you think about it, all the man has ever done is date Playboy Bunnies. He just keeps getting older, and they stay the same age.

#2 – Woody Allen – 73

Woody never beat around the bush when it came to his appetite for sex. In movies like Annie Hall and Everything You Ever Wanted to Know About Sex, he made very public his love for women. But even though he had a 17-year-old girlfriend in his 1979 film Manhattan, nobody expected Woody to turn to cradle robbing as severely as he did. In 1997, Woody wound up having an affair with — and then marrying — he and wife Mia Farrow’s adopted 27-year-old daughter, Soon-Yi Previn. Ten years later, they’re still married, and he’s still got 35 years on her.

#1 – Roman Polanski – 75

Mr. Polanski takes the top spot on our list since he’s the only man to have ever robbed the cradle so severely that he had to leave the country because of it. In 1978, he was arrested for — and pleaded guilty to — having a sexual encounter with a 13-year-old girl. Not only is that a 32 year age difference, it’s also illegal. Whoops! Instead of doing time for statutory rape, Roman fled to France. He hasn’t returned to America since, but he has taken a wife — French actress Emmanuelle Seigner, who happens to be 33 years younger than him. Looks like old habits die hard!