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28 Celebrities Who Are Notorious Cradle Robbers

Demi Moore

Demi (53) famously married the much younger Ashton Kutcher (pictured, 38) in 2005, and their marriage lasted until 2013, when some cheating allegations came out against Ashton. The couple divorced soon after this information came to light. In 2014, Demi began dating an even younger beau, Sean Friday (27), but they have since split up.

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The two men that this 57-year-old pop star married were actually fairly close to her age. Guy Ritchie was 10 years younger, and Sean Penn was only two years her junior. Yet, Madonna has recently taken to dating significantly younger men, including baseball player Alex Rodriguez (40), model Jesus Luz (29), and dancer Brahim Zaibat (pictured, 29).

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David Schwimmer

Friends star David (49) is known for his attraction to younger women. He married British singer Zoe Buckman (pictured, 25) in 2010, and before that, he dated actress Carla Alapont (32). Meanwhile, we’re still pining for him to be with Rachel.

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Linda Hogan

After her infamous split with Hulk Hogan, Linda (56) seemingly decided that younger men would be a better option for her. She decided to start dating her son’s friend, Charlie Hill (27). They even ended up getting engaged, which must have led to an awkward conversation with her son Nick, who was barely younger than Charlie.

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Hugh Hefner

There’s no possible way to even list all of the younger women Hugh (90) dated. Most of them were young enough to be his great-grandaughters. Gross. He famously dated Crystal Harris (pictured, 30), Kristina Shannon (26), Holly Madison (36), and Kendra Wilkinson (30), some of them at the same time!

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Courteney Cox

Courteney (51) and her former man David Arquette (44) aren’t that far apart in age, but apparently it was just enough to cause serious problems in their relationship. David opened up to Howard Stern about the pitfalls of their relationship, and apparently Courteney had become tired of feeling like his mother.

Woody Allen

Only five years after his separation from Mia Farrow, Woody (80) began dating Mia’s adopted daughter, Soon-Yi Previn (45). Undeniably creepy, and you can bet that Mia and Woody’s subsequent marriage definitely screwed up some family relationships. However, the couple is still going strong, even adopted two children of their own.

Roberto Cavalli

A famed Italian fashion designer, Roberto (75) began dating model Lina Nilsson (27) last year. That's a whopping 48-year age difference. He made headlines when he bought Lina an ancient Viking stronghold on a private Swedish island, so it’s obvious that she definitely isn’t in this relationship for the money.

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Steven Bauer

The Scarface actor (59) has been married and divorced three times, so last year Steven attempted to woo a new kind of woman: 19-year-old Lyda Loudon. Imagine how weird this must be for his own children, who are in their twenties, to have a potential stepmom who can’t even legally drink.

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Mel Gibson

Mel Gibson (60) can’t seem to ever escape controversy, but this time it’s not for any anti-Semitic comments. He is currently dating Rosalind Ross (25), but the couple isn’t seen together in public very often because Rosalind apparently does not like all of the negative attention she gets for dating someone who could be her grandfather.

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Jennifer Lopez

Jennifer Lopez doesn’t stay single long. After her split with Marc Anthony, she started dating younger men. Her most recent boyfriend is 25. That means that they have an 18-year age gap. J-Lo stated that “age, status, and opinions of others are irrelevant.” 

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Jerry Seinfeld

Jerry Seinfeld has a history of dating younger women. In 1999, he married Jessica Sklar when she was 28, and he was 45. Before that, he was in a relationship with a 17-year-old high school student named Shoshanna Lonstein. At the time, he was in his late 30s.

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Leonardo DiCaprio

Dear, Leo. He has a habit of dating women in their 20s, which was normal when he was also twenty-something. As he’s getting older – into his 40s – he’s still going for women that are in their early 20s. Many of them are Victoria Secret models. HIs current girlfriend is actually 21!

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Vivica A. Fox

Vivica A. Fox has a reputation of chasing younger men! She was engaged to a man who was 20 years younger. She’s also been seen dating men that are between 30 and 35 when she’s pushing 50. She also reportedly came out as being okay with being called a “cougar.”

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Russell Simmons

We couldn’t forget about Def Jam Recordings Founder Russell Simmons. Some of the women he dates aren’t even adults. In fact, he started dating his ex-wife Kimora Lee when she was just 17. Note: he was 35 at the time. His most recent relationship is with a 27-year-old. 

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James Woods

People are beginning to notice how James Woods has an eye for younger women – so much so that it became a moment of satire in an episode of Family Guy. At 66, he dated a woman that was 20 when he was 66. Before that was a 19-year-old. He also had an inappropriate encounter with Melanie Griffith when she was just 15 where he had to know if she had a boyfriend.

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Matthew McConaughey

Matthew is a dreamboat in the eyes of many women, but he’s currently taken by Camila Alves. This couple has an age gap of 14 years, but they’re quite happy. They have three children together and never stray far from each other.

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George Clooney

George Clooney may be one of the most attractive men alive, but women his age have a hard time dating him. Since the early 2000s, he’s preferred women that are in their 30s and 40s. Most of his recent girlfriends have had an age gap of 16 to 18 years.

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Sam Taylor-Wood

It was hot news a few years ago when Aaron Taylor-Johnson got together with Sam Taylor-Wood. When the two first got together, he was only 18, and they were already talking about starting a family. The two have a 23-year age gap between them.

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Eva Longoria

Eva Longoria is stunning, and it’s hard to believe that she’s close to 40. Longoria has a record of dating men that are younger than her including Tony Parker (7 years difference), Eduardo Cruz (10 years younger), and Mario Sanchez (12 years younger).

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Bruce Willis

Bruce Willis prefers to date younger women as long as they aren’t too famous. After his divorce from Demi Moore, he got engaged to Brooke Burns, who was 23 years younger. After that, he got married to Emma Heming who is also 23 years his junior.

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Jason Statham

Rosie Huntington-Whitely just recently got famous, but it didn’t take long for her to start dating another renowned star. Jason Statham began dating this model turned actor despite a 20-year age gap. They’re now married and are expecting their first baby!

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Johnny Depp

Johnny Depp hasn’t always gone after younger women, but Amber Heard changed that. The couple had a 23-year gap and had an incredibly tumultuous relationship. Depp was also with Vanessa Paradis, who was nine years his younger. That’s not as bad, but it should be noted.

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Joaquin Phoenix

Joaquin Phoenix is a little odd, in general. It’s only natural that his dating life matches that. His most recent girlfriend is only 20 years old, which is two decades younger than Phoenix. Then there’s his ex who was 11 years younger when they were dating. 

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Kris Jenner

Kris Jenner is a high-profile person that got into a relationship with a man, Corey Gamble, that’s 25 years younger. The pair had an easy-going relationship until they split. Jenner’s daughters seemed to want the couple to stay together so that a reunion may be in the works.

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Bradly Cooper

This star recently stated that he couldn’t date Jennifer Lawrence because they had a 16-year age difference, but his past says otherwise. He’s dated Suki Waterhouse, who was 17 years younger than Cooper. Dating younger women isn’t a problem.

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Halle Berry

Halle Berry has been in a relationship with Alex Da Kind since late 2017. A few people were surprised to learn that the pair has a 16-year gap. Before Alex, she dated Gabriel Aubry, who is nine years her junior. Not as bad, but we thought we should note it. 

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Robin Wright

Robin Wright split with Sean Penn and decided to date younger women. She’s been spotted with Ben Foster, who is 14 years younger, and Clement Giraudet, who is most certainly younger. Reporters don’t know his age just yet, but there’s a definite age gap between them.

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Priyanka Chopra

11 years may sound like a big age difference between Priyanka Chopra and her younger beau, Nick Jonas, but according to the couple, they're not that concerned with it. In fact, it's rumored that Jonas enjoys the company of older women anyways. 


Ryan Reynolds

Celeb power couple Ryan Reynolds and Blake Lively met when the young actress was just 22--making for an age difference of 11 years between them. That being said, Reynolds was only 33 at the time, which isn't exactly over-the-hill itself. 

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When Ellen and Portia de Rossi got together in 2004, there was a 15-year gap between them. But regardless of the age difference, the two have happily begin together ever since. 



There may be a gap of 12 years between Jay-Z and Beyonce, but really, that is trivial at this point. Both members of this power couple have proven to be equally successful and iconic in pretty much everything they do. 

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Michael Douglas

Even though long-time couple Michael Douglas and Catherine Zeta-Jones have a 25-year gap between their ages, they do share one time-based thing in common: they were both born on September 25. 


Olivier Sarkozy

You know you're an odd couple when a 17-year age gap is the least remarkable thing about you. What's even stranger about the relationship between Olivier Sarkozy and Mary-Kate Olsen is that Sarkozy's half-brother is Nicolas Sarkozy--former president of France. Oh, and the fact that they allegedly had bowls of cigarettes laying out at their wedding. 


William H. Macy

When William H. Macy met his future wife, Felicity Huffman, he was 12 years older than her. Although, these days, the two are probably more well-known for their legal troubles as opposed to their age gap. 

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Harrison Ford

When Harrison Ford was saving the galaxy as Han Solo in 1977, there's a good chance his future wife, Calista Flockheart, was watching along as a wide-eyed teenager. However, the couple doesn't seem that troubled by their 22-year age difference--they married in 2009 and have an adopted son together. 

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Alec Baldwin

When Alec Baldwin met his wife, Hilaria, they were 26 years apart. But what's really strange about this relationship is how they met--she was a yoga instructor at the time. Can you imagine Alec Baldwin doing yoga? Neither can we. 


Billy Joel

There is a 33-year age difference between Billy Joel and his fourth (and current wife), Alexis Roderick. Age truly is nothing but a number to them, because the couple seems to be going strong and even has two daughters. 

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Rod Stewart

There is a 27-year age gap between Rod Stewart and his third wife, Penny Lancaster, but that didn't stop the couple from tying the knot in 2007. Apparently, the third time really is the charm, because the couple is still together today. 


David Cross

The 19-year gap between spouses David Cross and Amber Tamblyn is only intensified by the fact that she looks perpetually 25 and he looks perpetually like a wizened sea captain.