Top 05 Famous Cradle Robbers

5. Jack Nicholson

    So, he's been dating women younger than his youngest daughter (both born in 1963, she's about nine months younger than Jennifer) since nearly two decades ago in 1989 when he started a relationship with Rebecca Broussard. I give Jack 9 cribs). Keep in mind that she was born in 1937, so while some of her partners don't look shockingly young, many of her relationships still fall into the cradle-robbery category. For example, when they got together in 1973, Anjelica Huston was 22 (he was 36). His most recent relationship was with Lara Flynn Boyle, when it ended when he was 31 and she was 64. He's 71 now, so even if he's 42, he'll technically rob the cradle. It's a pretty old crib, which is why it's not higher on the list.

  4. Joan Collins

  Joan Collins is currently married to a man who is 32 years her junior (she's 43, he's 75). When asked about the age difference between him and Percy Gibson, Collins replied: "If it dies, it dies." ('Joan Collins', Wikipedia.) She deserves to be on this list just for this comeback, but she left a few empty cradles behind:

  Ron Hurlstone - When they started dating in 1987, she was 29 and he was 56 (the relationship lasted 14 years).

  Peter Holm - They were married for 4 years in 1983 when he was 36 and she was 50.

  Joan dated Charlie Chaplin's son for a while, but it didn't work out because he was seven years older than her. I guess crib stealing isn't genetic - because look who's next on our list!

  3. Charlie Chaplin

  Charlie Chaplin's oldest wife, Paulette Goddard, was in her early 20s when they married in 1936. Chaplin was 47 years old. There is actually some doubt as to whether or not they are actually married, but fortunately that is not one of the criteria for the crib. robbery so I'm still listing it.

  Mildred Harris was 16 when she married Charlie Chaplin (29) in 1918.

  Lillita McMurray (stage name Lita Gray) was 16 when 36-year-old Chaplin married him in 1924.

  Oona O'Neil - Chaplin married O'Neil when she was 17 and he was 56 (apparently by this time she had already dated Orson Welles and J.D. Salinger!). They were together for richer and poorer, through sickness and in health, as they were kicked out of the United States and later became ill. He stayed with her until his death in 1977. He was 88 years old and they were together for 32 years.

  Chaplin robbed up to 8 more cribs, but I won't list them all here. Unless you're a huge Chaplin fan, you might not recognize any of the names.

  I give Chaplin 16 cribs because he married two 16-year-olds. (Also, 16+16 = 32 is how long with O'Neill.)

  Both Woods and Allen won the Golden Cradle

  2. James Woods

  James Woods is famous for his crib robbery, but his relationship history was a bit of a mystery. I generally had trouble finding any information about his past and wondered if he had some kind of censorship control over the Internet. That is, until he came across the popular website hookups.com, which listed 17 different partners for him. Some of her ex-boyfriends:

 

  Elizabeth Hilden – I'm curious because according to popular hookups.com, if Elizabeth were 34 now, she would have been 16 when we met in 1990, but she was a Playboy model at the time, and I'm serious about letting 16-year-olds model for them Do you doubt? At least without parental consent, I guess. Yuck.

1. Woody Allen

  Actually, I have to stand up for Allen on this one because it was 1954 and I think it was more acceptable to marry a 16-year-old (Woody was 19. 19 divided by 2 plus 7 is 16.5, so technically it's still robbery.cradle according to Eq.). That's close, the threshold is 16.5 according to the equation, and maybe Harlene was halfway to her 17th birthday on her wedding day, so it wouldn't even count. I'm willing to be generous here, as Allen has enough cradles to rightfully earn his place at the top of the list in the future.

  Diane Keaton – This shocked me for some reason, probably because I was so young when I saw Annie Hall that I thought everyone over 20 was about the same age. When they got together in 1970, Allen was 35 and Keaton was 24. Not too shocking yet, but of course you already know who's coming next...

  Stacey Nelkin - Have you seen Manhattan? It appears to be based on Allen's relationship with Stacey, who was a 17-year-old high school student at the time. Interesting side note: Nelkin performed in Annie Hall, but ended up on the cutting room floor. Nearly 20 years later, Allen cast Stacey Nelkin in Bullets Over Broadway, and at the same time his relationship with Soon-Yi came to light, his ex-girlfriend Mia Farrow accused him of molesting her 7-year-old daughter. His affair with Stacey Nelkin was never publicly acknowledged by Allen - perhaps the role in his film encouraged Nelkin, an actor who had only appeared in various TV series and Halloween III until then, to keep quiet...?

  Soon-Yi Previn – When her relationship with Soon-Yi Previn became public, everyone was forced to admit to Woody's crib-robbing ways. He and Mia Farrow were together for twelve years and Soon-Yi was Mia's daughter from a previous marriage. Woody and Mia were still together when Woody found Soon-Yi's nude photos. Woody is 35 years older than Soon-Yi (he was 27 and she was 61 when they married in 1997).