Top 10 Celebrities Who Have Played Couples More Than Once

Three movies. Three decades. Two really good friends. Since working together on The Wedding Singer in the ‘90s, Sandler and Barrymore have gotten back together to film one movie every decade, and even sang about it on The Tonight Show Starring Jimmy Fallon. There has never been a romantic connection off-screen between the two – but, Sandler's wife does say she loves Drew... – and that's probably why they continue to work together and stay such good friends. It's almost surprising that they've only made three movies together.

With all the fuss over La La Land, the 2016 Oscar-winning film starring Gosling and Stone in the lead roles, it's easy to forget that this wasn't the first time the young actors played a couple. In fact, La La Land was actually the third time Gosling and Stone starred opposite one another since 2010. The first film was a comedy, the second a thriller, and the third a musical, proving not only that Ryan and Emma have good chemistry, but also that they are both extremely versatile as actors. Chances are, La La Land won't be the last time we'll see them work together either.

Jack and Rose's tragic romance in Titanic is far too memorable for their actors to ever work alongside each other again, right? Wrong. In 2008, over 10 years after Titanic's release, the two teamed up again, playing a couple in the critically acclaimed film Revolutionary Road, proving that casting these two together is a good idea. The only thing perhaps better than their performances is Kate and Leo's real life friendship, and the tremendous support they show for each other's careers.

After starring alongside each other in two huge romantic classics, Sleepless in Seattle and You've Got Mail, these two just have to accept that their names will forever be linked together. Still, most people don't even realize that they played a couple in not just two but three films, the first being Joe Versus the Volcano, which was released years before Sleepless in Seattle. Tom even had a brief on-screen reunion with Meg in Ithaca, a film she directed and cameo'd in in 2015.

The ‘90s began and ended with films starring these two, with Pretty Woman coming out in 1990 and their second film, Runaway Bride, arriving in 1999 to bookend the decade. Of course everyone knows the former rom com classic for Roberts's portrayal of a hooker with a heart of gold, but what also made the film what it was, was the blend of Gere's serious attitude with Julia's lightheartedness. It's no wonder they tried duplicating the success of the first film with the second. Though they haven't made a movie together in over a decade, there's always the chance, as the two remain close friends.

It was rumored that Burton didn't much like Elizabeth Taylor when they first met on the set of Cleopatra, but things obviously quickly changed because not only did they go on to make ten more movies together, but they also married in real life – twice. When they first got together, they were both already married to other people, so they divorced them and married each other soon after. But then they eventually divorced themselves, only to marry again a year later. Annnnnd then divorced again. Okay, so their relationship might not have worked out, but at least a few decent movies came out of it.

Humphrey Bogart was known as somewhat of a ladies man and was married not once, not twice, but three times by the time he'd met Lauren Bacall while filming their first movie together. Even though he was 25 years her senior, the two began a relationship that was more than just professional. Bogart filed for divorce from his then-wife Mayo Methot and married Bacall in February of 1945, the year they made their second film, The Big Sleep. They remained married until Bogart's death in 1957 and made two more movies together along the way.

Lauren Bacall's good friend Katharine Hepburn was yet another actress who fell in love on set. She and Spencer Tracy acted together in nine films. Though he was only estranged and never officially divorced from his wife, that didn't stop him and Katharine from also pursuing a relationship outside of work, one that lasted over 26 years until Tracy's death in 1967. While they never had children, or married, in the years after his death Hepburn stated she was happy just being with him.

Here are two names that cannot be said without thinking of the other. The famous duo was never romantically involved, but their on-screen career together lasted over 15 years, so it’s no wonder people can't help but think of them as a couple. Both Fred and Ginger began their dancing and acting careers as solo artists, but after appearing in Flying Down to Rio together, they were seldom apart. In fact, their next joint film saw them in lead roles. Throughout their career, they each worked on solo projects as well, but never quite experienced the same amount of popularity alone that they had over the course of nine films together.


Before we reveal our number one pick, here are a few honorable mentions.



Brad Pitt & Angelina Jolie


Kurt Russell & Goldie Hawn


Michael Douglas & Kathleen Turner

Between the years of 1982 and 1992, Mia Farrow starred in 13 of Allen's films, which probably had something to do with the fact that the two had been in a relationship since the late ‘70s-early ‘80s. Meanwhile, the end of their cinematic partnership coincided with their controversial break up. This wasn't the first time Allen dated a co-star – he and Diane Keaton dated briefly – but it was definitely the most scandalous. Because, although Mia and Woody made a good on-screen couple, the latter felt that there was more chemistry between himself and Farrow's adopted daughter Soon-Yi, who he not only left Farrow for but would go on to marry instead.