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George Clooney -

George Clooney was 53 when he walked down the aisle with human rights lawyer Amal Alamuddin in 2014. The actor had been widely considered Hollywood's most eligible bachelor since his divorce from first wife Talia Balsam in 1993. His marriage to Amal is still going strong.

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Harrison Ford -

Hollywood hot stuff Harrison Ford married 'Allie McBeal' star Calista Flockhart in 2010. Although it was youthful Flockhart's first marriage, it wasn't Ford's first rodeo: he had been married twice before.

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Harrison Ford -

The 22-year age gap hasn't stopped the couple from finding wedded bliss. They're still a handsome Hollywood couple more than 10 years later.

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Ellen DeGeneres -

Comedian and TV host Ellen DeGeneres was 50 when she got hitched to her long-term girlfriend, actress Portia de Rossi, in 2008.

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The couple wed shortly after same-sex marriage was legalized in the United States, and are still happily married more than a decade later.

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Paul McCartney -

Paul McCartney was 69 and had been once-widowed, once-divorced when he married American businesswoman Nancy Shevell in 2011. The transatlantic couple are still happily married.

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Paul McCartney -

McCartney's previous marriage to model and activist Heather Mills ended acrimoniously in 2008 after six years of marriage. He was 59 when they wed.

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Paul McCartney -

McCartney lost his first wife, photographer and animal rights campaigner Linda McCartney, to cancer in 1998. The pair had been married since 1969, and she was just 56 when she passed away.

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Elton John -

Elton John blazed a trail when he wed long-term partner David Furnish in 2014  shortly after the legalization of same-sex marriage in the UK. They had previously held a civil ceremony in 2005.

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Elton John -

The couple had been a long-established presence on the celebrity party scene for decades before their wedding.

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Elton John -

Although it was Elton John's first same-sex marriage, it wasn't his first trip down the aisle. The singer married German sound engineer Renate Blauel in 1984 before they divorced four years later.

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Barbra Streisand -

Singing legend Barbra Streisand had been divorced from first husband Elliott Gould for nearly 30 years when she married actor James Brolin in 1998. She was 56 at the time.

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The low-profile Hollywood pair have kept their marriage going strong for over two decades.

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Warren Beatty -

Warren Beatty didn't get married and start a family until his mid-fifities. The actor had been a long-time eligible bachelor when he met actress Annette Bening in 1991 on set of the film 'Bugsy.' Beatty said it took him “seven or eight seconds" to realize she was the one. The couple were married in 1992.

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Warren Beatty -

Beatty had previously been hard to pin down.  Despite high-profile romances with everybody from Madonna to actress Natalie Wood (pictured), he had never previously been tempted to say "I do."

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Warren Beatty -

It was worth the wait: Warren Beatty and Annette Bening are seen as one of the most solid couples in showbusiness, and have four children together.

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George Takei -

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George Takei -

The happy couple were among the first in Hollywood to apply for a marriage license once same-sex marriage was legalized, and remain happily wed.

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Brad Pitt -

Brad Pitt was 50 when he married Angelina Jolie in 2014 after several years of dating. Both had been married before.

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Brad Pitt -

Angelina Jolie had two previous weddings behind her: she was married to her 'Hackers' (1995) co-star Johnny Lee Miller from 1996 to 1999, and to actor Billy Bob Thornton from 2000 to 2003.  Brad Pitt was infamously still married to Jennifer Aniston when Brangelina met on the set of 'Mr. & Mrs. Smith' (2005).

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Brad Pitt -

While the couple were Hollywood royalty for a while, and have several children together, the marriage ended up in bitter court wranglings.

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RuPaul -

RuPaul was 56 when he got hitched to partner Georges LeBar in 2017—23 years to the date that the couple first met.

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RuPaul -

The 'Drag Race' host and limelight-shirking LeBar appear very much in love, although Ru cited financial reasons as the main deciding factor for making things official.

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Robert Redford -

Actor Robert Redford had been divorced from first wife Lola Van Wagenen for more than a decade when he met artist Sibylle Szaggars in 1996. By the time the couple tied the knot in 2009, Redford was 73 years old.

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Robert Redford -

The pair married in Szaggars' native Germany and have cut a dash together on the red carpet ever since.

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Prince Albert of Monaco -

Proving that even real-life royals sometimes have to wait for their happy ending, Prince Albert of Monaco was 53 before he wed South African Olympic swimmer Charlene Wittstock in 2011.

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The couple have three children together, and despite persistent rumors of marriage problems, are still officially together.

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Vanessa Williams -

Third time's the charm for Vanessa Williams: the singer and actress had been married twice before she got hitched aged 52 to current husband, real estate agent Jim Skrip.

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Vanessa Williams -

Williams has four children from her two previous marriages: three from her 10-year marriage to Ramon Hervey II, and one from her second marriage to then-basketball star Rick Fox. 

Sources:(People) (Showbiz Cheat Sheet) (Insider) (The Wall Street Journal) (BBC) (Time)

See also: Do relationships with big age gaps work?

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