Robbing the Cradle! 17 Celebs Who Dated Way Younger People

When it comes to Hollywood and the rich and famous, robbing the cradle takes on a whole new meaning. After all, Tinseltown is nothing if not known for (mostly) men who date and marry partners who are decades younger. There have been a few women who have robbed the cradle, but largely, it is an older male-younger female dynamic.

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So who are 15 celebrity couples with huge age differences?

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The age differences on this list run from 20 years and climb all the way up to six decades! Yes, there is a celeb who robbed the cradle with a 60 year age difference. Many of these partners are both famous … think Michael Douglas and Catherine Zeta-Jones, with their 25 year difference in age.

Age Difference: 15 years

When Demi Moore and Ashton Kutcher got married in 2005, their 15 year age difference didn’t seem to be an issue. Yet, after eight years, their marriage ended. As Radar Online reported, it was likely due to accusations that Ashton cheated on Demi with a girl he met in San Diego. No one can know why someone strays, but in many cases it leads to divorce, and Demi and Ashton’s legal split was tough on both of them according to Radar Online.

Age Difference: 20 years

When Pete Davidson and Ariana Grande broke up, the SNL star seemed to take it truly hard. There was even concern that he was suicidal, as Radar Online reported. But nothing mends the heart like a new relationship. Pete met Kate Beckinsale at a Golden Globes party in January of 2019 and the two have been inseparable ever since. Their age difference does not appear to bother them. When you have obvious physical chemistry, your date of birth doesn’t matter one bit. Let’s see where these two go … whether they last or fall into the celebrity couple dustbin. Judging by that makeout session at the New York Rangers game, as seen in OK! Magazine, they are off to a passionate start.

Age Difference: 22 years

When Harrison Ford and Calista Flockhart started dating she was 38 and he was 60. The two got married on June 15, 2010 and are still enjoying wedded bliss. In fact, to celebrate their eighth wedding anniversary, Radar Online published details of the “splashy wedding she always wanted,” given to her by Harrison.

Age Difference: 25 years

On November 18, 2000, Hollywood legend Michael married his sweetheart, Welsh actress Catherine. Their 25 year age difference was not an issue while dating, and it hasn’t been one to this day. They’ve been through good times — raising two kids — and tough times but risen above it all. Us Weekly reported that Catherine was “devastated” by the sexual misconduct allegations leveled against Michael. How’d they respond? The family got even closer.

Age Difference: 25 years

Another celebrity couple with a 25 year age difference is TV superstar Kelsey Grammer and his bride, Kayte Walsh. Kelsey had recently emerged from a nasty divorce from Real Housewives of Beverly Hills star Camille Grammer who 14 years younger. One could see that after experiencing the horrors of a tangled divorce walking down the aisle might not be one of your top priorities. But the star of Cheers and Frasier put a ring on the finger of Kayte in February of 2011. Kayte was expecting their first child at the time, and judging by the photos that Radar Online ran of their big day, it was pure happiness all around!

Age Difference: 26 years

The relationship fallout of Kim Basinger and Alec Baldwin was particularly “nasty” as Kim once told Closer Weekly. There was also that notorious voicemail that went public where Alec berated his daughter, Ireland, and called her a pig. Later, as Radar Online reported, Alec’s daughter called the incident “no big deal.” Alec has mellowed over the years, and it could be attributed to his relationship with yoga instructor Hilaria Thomas. He also looks better than he has in years marriage (and yoga) suit him well.

Age Difference: 26 years

Larry King has been married multiple times. Well, specifically, the talk show host has been hitched eight times! Larry might have just found the real thing because he has been happily married to Shawn Southwick since September 5, 1997. The man and the actress have an age difference of 26 years. The secret to their long marriage? Perhaps, as Radar Online had reported, they have an open marriage.

Age Difference: 27 years

How many rock star marriages work? For every Pat Benatar and Neil Giraldo, there are thousands who have imploded. Another success story showed up with Rod Stewart marrying Penny Lancaster in June of 2007. The biggest surprise with this relationship is that they’re still together! In fact, they are so in love with each other that they renewed their vows during their 10th wedding anniversary, as reported in Us Weekly.

Age Difference: 27 years

William Shatner boldly went where many have gone before — to the chapel to get married — to Elizabeth Anderson Martin in February of 2001. The Star Trek star and Elizabeth have a 27 year difference. Radar Online reported that William had suicidal thoughts (detailed in his tell-all book) after his previous wife, Nerine Kidd, drowned. He was #blessed to be able to find love once again.

Age Difference: 30 years

When Frank Sinatra married Mia Farrow, the singing icon was 51 and she was merely 21. That’s 30 years. Sadly for Mia, the joy of being married to Old Blue Eyes faded quickly. They divorced after two years and one month. Although they never had children officially, rumors have swirled for years that Mia’s son Ronan Farrow is a product of their union and not hers to Woody Allen — as reported in Closer Weekly. Ronan and Frank do share similar features … just saying! In fact, Allen was quoted as saying "I wouldn't bet my life" that Ronan was his son.

Age Difference: 32 years

British icon Joan Collins wed Percy Gibson and like a surprisingly high number of couples on this list, they are still married. Percy, who was born in Peru, is a television and film producer, and her fifth husband. Joan may have gained international fame with her devilishly delicious turn in the ‘80s prime time soap Dynasty, but she has been dropping jaws with her work since the ‘60s. The secret to their marriage, Joan told Closer Weekly, is “always be forgiving.”

Age Difference: 35 years

When Billy Joel and Alexis Roderick got hitched, it was his fourth saunter down the aisle. Billy, who was previously married to model Christie Brinkley, joined the old-marrying-young club for the second time. The "Piano Man" married chef Katie Lee, 32 years his junior, and failed to go the distance. As Closer Weekly reported, the pair split up in 2010. Billy and Alexis have been married since 2015 and set off some serious fireworks by getting married on July 4! Radar Online reported that in October of 2017 the couple welcomed Billy’s third daughter at his young age of 68.

Age Difference: 35 years

Tying Billy and Alexis in the age difference department: Clint Eastwood and Dina Ruiz! The legendary actor/director/producer married the actress/journalist in March of 1996. The pair were married for 18 years when they split three days before Christmas in 2014. Bah humbug! As reported in Us Weekly, Dina has found love again — marrying basketball coach Scott Fisher.

Age Difference: 37 years

One of the most scandalous members of this club was the marriage of film director Woody Allen and Soon Yi Previn. Soon Yi was Woody’s stepdaughter when they allegedly had an affair under the nose of her mother and Woody’s then wife, Mia. The couple had an age gap of 37 years. The public, as reported to Radar Online, was shocked by the turn of events in the Woody-Mia marriage. Knowing that Soon Yi was 19 when she married Woody, who was 56, many wondered how close to her 18th birthday they started being amorous.

Age Difference: 60 years

The winner of the celebrity-robbing-the-cradle club probably was not much of a shock, given the love Playboy founder Hugh Hefner had for frolicking with women much younger than him. Still, when Hugh and Crystal Harris got married, it was six decades of life that separated the two. The secret to his long life may have been this robbing the cradle. As reported in OK!, a doctor is quoted as saying that Hugh’s promiscuity fueled a powerful heart and that allowed him to live fabulously to the age of 91.