Top 10 Cradle Robbers


I can think of lots of reasons why people may be interested in ‘robbing the cradle’. Perhaps the cradle robber is in denial about how old he or she really is. I know I often realize with a shock that I am over 30… imagine what it would be to be 60… or 80? Others might think that they look young and beautiful because they are standing next to someone who is young and beautiful; however, I would like to point out that if you want to make yourself look good it’s smarter to stand next to someone who is LESS good looking than you.

While the rich and famous get the most publicity, they are not the only ones cradle robbing. It might seem like it but that’s only because their relationships are more newsworthy than the average person. During my research for this article I found online communities and support groups for lots of every day people involved in this type of relationship. They describe the nature of their relationships as ‘age-gap’ rather than cradle robbing (sounds nicer). There are also less subtle groups, such as and full of young ladies (and men) who are eager to date a cradle robber.

Do you know a cradle robber? Or perhaps you are one? Read the guidelines  and you can do the math yourself to see if you fit the guidelines.

A cradle robber is a person who taps people significantly younger than themselves. If X is the older person’s age then they are labeled a cradle robber if they date a person who is less than half of their age plus 7 years. But for this function to work, X must be greater than or equal to 18, as dictated by Urban Dictionary at

Example: Demi More was 42 when she married Ashton Kutcher (27) in 2005. 42 divided by 2, plus 7 is 28, but Ashton was 27 so that makes Demi a cradle robber (by the way, way to go, Demi!).

I struggled with placing the people on this list in order. It was hard to decide who was more of a cradle robber: is it someone who has been in more relationships or someone who really stretches that age gap? If you can make a good argument for why the order should be different, I’ll listen. Here is what I decided:

10. Demi Moore

Demi Moore & Ashton Kutcher

Demi Moore & Ashton Kutcher

When Demi Moore was busy being ‘Jules’ in St. Elmo’s fire (1985), Ashton Kutcher was 7 years old. He’s 16 years younger than her and they have been together for 5 years. Everyone knows about Demi and Ashton and, before that, Demi and Bruce. Here are two more relationships that land helped to land Demi Moore on our list:

  • Oliver Withcomb – Moore dated him in 2001. He’s a martial arts instructor and seven years younger than her.
  • Leonardo DiCaprio – They dated in 1998. He was 24 and she was 36.

I’m only giving her one cradle because the other two relationships were very short. Also, it seems like Kutcher and Moore are very happy and I think we’re all ready to leave them alone already.

9. Michael Douglas

Michael Douglas & Catherine Zeta-Jones

Michael Douglas & Catherine Zeta-Jones

Michael Douglas’ first wife Diandra Luker was either 19 or 21, depending on which source you want to believe, when they were married in 1977. He was 33. Their divorce was official in 2000, 23 years later. That same year, Douglas married Catherine Zeta-Jones (she was 31, he was 56). They share the same birthday (Sept 25) so they are exactly 25 years apart.

Douglas is getting a cradle for each of his cradle robbing marriages plus one half of a cradle because they were both pretty close to half his age at the time.

8. Rod Stewart

Rod Stewart & Penny Lancaster-Stewart

Rod Stewart & Penny Lancaster-Stewart

Rod Stewart deserves at least 3 empty cradles:

  • Penny Lancaster-Stewart – 26 years apart, Rod married Penny in 2007 (He was 62 and she was 36.)
  • Rachel Hunter – He was 45 and she was 21 when they got together in 1990.
  • Kelly Emberg – He was 38 and she was 24 when they got together in 1983.

7. Billy Joel

Billy Joel & Katie Lee Joel

Billy Joel & Katie Lee Joel

Billy Joel’s wives keep getting younger as he gets older. His most famous wife, Christie Brinkley, was only 5 years younger than him. Now he is married to Katie Lee Joel, 32 years younger than him. They got married in 2004 when she was 23 and he was 55.

Joel earns 4 cradles because his new wife is only 4 years older than his daughter (Alexa Ray Joel, b.1985 vs. Katie Lee Joel, b.1981)

6. Nicolas Cage

Nicolas Cage & Aice Kim

He married Alice Kim when she was 19 and he was 40. No need to add 7 to figure out that this one definitely falls into the cradle-robbing category, so I’m just going to give him 7 cradles instead.

She was a waitress when they met, which is weird because he met his ex-wife Patricia Arquette in a deli… maybe he just really likes food and not teenagers…

If you’re like me, you’re in your thirties and you’ve had a crush on Nicolas Cage since ‘Valley Girl’. Well, Cage and Kim have been married for over four years now but don’t lose hope – he has an 18 year old son – maybe it’s time to redirect that crush and do some cradle robbing of your own!

5. Jack Nicholson

Jack Nicholson & Lara Flynn Boyle

Jack Nicholson & Lara Flynn Boyle

Jack Nicholson’s eldest child, Jennifer Nicholson was born in 1963. So he has been dating women younger than his little girl since he hooked up with Rebecca Broussard almost twenty years ago in 1989 (both born in 1963, she’s about nine months younger than Jennifer so I’m giving Jack 9 cradles). Keep in mind, he was born in 1937, so even though some of his partners don’t seem shockingly young, many of his relationships still fall into the cradle-robbing category. For example, Anjelica Huston was 22 when they got together in 1973 (he was 36). His most recent relationship was with Lara Flynn Boyle, she was 31 when it ended and he was 64. He is now 71 so even if he dates a 42 year old, he will technically be robbing the cradle. That’s a pretty old cradle, that’s why he’s not higher on the list.

4. Joan Collins

Joan Collins & Peter Holm

Joan Collins & Peter Holm

Joan Collins is currently married to a man that is 32 years younger than her (he is 43, she is 75). When asked about the age difference between her and Percy Gibson, Collins replied, “If he dies, he dies”. (‘Joan Collins’, Wikipedia.) She deserves to be on this list just for that kickass comeback, but she has left a few other empty cradles behind her:

  • Ron Hurlstone – He was 29 and she was 56 when they started dating in 1987 (the relationship lasted 14 years).
  • Peter Holm – They were married for 4 years, beginning in 1983 when he was 36 and she was 50.

Joan dated Charlie Chaplin’s son for a while but he doesn’t qualify because he was actually seven years older than her. I guess cradle-robbing isn’t genetic – because look who is next on our list!

3. Charlie Chaplin

Charlie Chaplin & Oon O'neil

Charlie Chaplin & Oon O

Charlie Chaplin’s oldest wife, Paulette Goddard, was in her early 20’s when they got married in 1936. Chaplin was 47. Actually, there is some doubt as to whether they were really married or not, but luckily that’s not one of the criterion for cradle robbing so I’m still listing her.

  • Mildred Harris was 16 in 1918 when she married Charlie Chaplin (29).
  • Lillita McMurray (stage name Lita Grey) was 16 when a 36-year-old Chaplin married her in 1924.
  • Oona O’Neil – Chaplin married O’Neil when she was 17 and he was 56 (apparently she had already dated Orson Welles and J.D. Salinger by this time!). They were together, for richer and poorer and through sickness and good health, literally, as he was kicked out of the US and he became ill later on. She stayed with him until he passed away in 1977. He was 88 and they were together for 32 years.

Chaplin robbed up to as many as 8 more cradles but I won’t list them all here. You wouldn’t recognize any of the names unless you are a huge Chaplin fan.

I’m giving Chaplin 16 cradles because he married two 16 year-olds in a row. (Also, 16+16 = 32 which is how long he was with O’Neill.)

Both Woods and Allen have earned the Golden Cradle

2. James Woods

James Woods & Alexis Thorpe

James Woods & Alexis Thorpe

James Woods has a reputation for cradle robbing but his relationship history was a bit of a mystery. I was having problems finding any information about his exes at all and wondering if he had some sort of censorship control over the Internet. That is, until I stumbled across a website called famous that lists 17 different partners for him. His current girlfriend, Ashley Madison, is 22 years old (that’s 39 years younger than him). Here are a few of his exes:

  • Alexis Thorpe – 20 years old when they dated in 2000. He was 53.
  • Missy Crider – 23 years old when they were engaged three years earlier in 1997.
  • Heather Graham – 22 years old when they dated in 1992 (he was 45.)
  • Elizabeth Hilden – I’m wondering about this one because, according to famous, Elizabeth would have been 16 years old when they dated in 1990 if she is 34 now but she was a Playboy model at the time and I’m seriously doubting that they let 16 year-olds model for them? At least not without a parent’s consent, I guess. Yuck.

1. Woody Allen

Woody Allen & Soon-Yi Previn

Woody Allen & Soon-Yi Previn

Allen started early when he married 16-year-old Harlene Rosen. Actually, I have to stand up for Allen on this one because it was 1954 and I think marrying a 16 year old was more acceptable back then (Woody was 19 years old. 19 divided by 2 plus 7 is 16.5 so technically this is still robbing the cradle according to the equation.). This is a close one, the limit is 16.5 according to the equation and perhaps Harlene was halfway to her 17th birthday on their wedding day, so then it wouldn’t count at all. I’m willing to be generous here because Allen has more the enough cradles in his future to still rightfully earn his place at the top of the list.

  • Diane Keaton – This one shocked me for some reason, I guess I was so young when I saw Annie Hall that I just thought anyone over 20 was pretty much the same age. Allen was 35 and Keaton was 24 when they got together in 1970. Still not very shocking, but of course, you already know who’s coming later on…
  • Stacey Nelkin – Have you seen the movie Manhattan? Well apparently it’s based on Allen’s relationship with Stacey, who was a 17-year-old high school student at the time. Interesting extra information: Nelkin acted in Annie Hall but ended up on the cutting room floor. Almost 20 years later, Allen gave Stacey Nelkin a role in Bullets Over Broadway right around the same time his relationship with Soon-Yi became known and his ex-girlfriend Mia Farrow accused him of molesting their 7-year-old daughter. His relationship with Stacey Nelkin has never been publicly acknowledged by Allen – perhaps a role in his movie encouraged Nelkin, an actor who had only appeared on various TV series and Halloween III up until then, to keep quiet…?
  • Soon-Yi Previn – Everyone was forced to acknowledge Woody’s cradle robbing ways when his relationship with Soon-Yi Previn became public. He and Mia Farrow were together for twelve years and Soon-Yi was Mia’s daughter from an earlier marriage. Woody and Mia were still together when she found nude photos of Soon-Yi in Woody’s possession. Woody is 35 Years older than Soon-Yi (she was 27 and he was 61 when they were married in 1997). Eleven years later they are still together and have two daughters.


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  1. i’m guessing this is just for actors/actressses but what about celine dion and her hubby renee angelil? he was her manager when she was discovered at either 13 or 14 and he was in his 40’s…they have a 26 year age difference and have been married since 1994..and nobody thought this was really creepy or weird? not quite the courtney stodden situation…but close.

  2. So Jack Nicholson in “Something’s Gotta Give” was playing himself – an old cradle robber 😀

  3. Can't leave out Clint Eastwood + Dina Ruiz!

    * Clint Eastwood Jr: Born May 31, 1930

    * Dina Ruiz: Born 1965

    – They got married in 1996

    ~Ages when married: 66 V.S. 31 : 66/2+7 = 40 (Clint) V.S. 31 (Dina) = big-time cradle robber

    Today: 80 V.S. 45 : 80/2+7 = 47 (Clint) V.S. 45 (Dina) = 16 years later, still would be a cradle robber today!

    *** "Extra cradle points": Clint's first child (daughter, born 1964) is older than his wife (Dina).

  4. Tanya Bennett on

    Hmmmm – I don't think J. Howard Marshall is considered a cradle robber so much as Anna Nicole Smith is considered a gold digger… The Great Balls of Fire singer Jerry Lee Lewis was 23 when he married 13 year old Myra Gale Brown so he fits into the cradle robber category. I took the following factors into account when I decided not to include him on this list: it was 1957 when they got married, his own sister got married when she was 14, and he didn't continue cradle robbing after their divorce 13 years later. What I find more interesting: 1) he married Myra before his divorce to his previous wife was final 2) Myra was his 2nd cousin.

    So, if I ever make a list of top ten bigamists or top ten kissing cousins, I think Jerry Lee Lewis will definitely be on there (not to mention top ten rockabilly musicians of all time!)

  5. wat about that guy who married his 13 yr old cousin i forget his name but he sings great balls of fire

  6. What about!..

    Ana Nicole Smith – J. Howard Marshall?

    he was 63 years her senior

  7. helo! The babes are here! This is my favorite site to visit. I make sure I am alone in case I get too hot. Post your favorite link here.

  8. @Allison – I answer that one up in the comments posted November 18 (above) – he does seem like a likely contender but I think the 10 on my list outrank even him…

  9. Tanya Bennett on

    I can't find any information about Hayley Mills being a cradle robber, but her first husband Roy Boulting was: he was 33 years older than her when they got married. The marriage lasted 7 years. According to his obituary, Boulting was married 5 times – not sure about the ages of his other wives at this time…

  10. Caulfield and Mills' relationship definitely meets the criteria. Yet, while it was Juliet Mills' third marriage, it was the first cradle she robbed (she was 39, he was 21). One cradle isn't enough to get her on the list but it's always nice to see some women cradle robbers for a change! They have been married for almost 29 years…

  11. I know I had him on my shortlist but I knocked him off because to me his cradle-robbing is part of his profession. He didn't start off dating super young women, it was just that he got older while the models that he employed did not. His first wife Mildred Williams was 23 when they got married in 1949 (Hugh was the same same age) and they were married for 10 years. I don't know that any of this indicates that he is a cradle-robber by nature; more just by convenience… In fact, according to Wikipedia, his first wife confessed to cheating on him early in their relationship so perhaps he was just desperately trying to prove himself and not the genuine playboy he pretended to be…