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Michael Keaton is a man of many roles. Playing characters that range from comedy to superhero to villain, the actor has proven himself as a highly versatile performer.

Many may not remember that Keaton had a 5 1/2-year romance with this actress from the iconic NBC sitcom Friends.

Michael Keaton | Gregg DeGuire/FilmMagic

Memorable roles

According to IMDb, Keaton’s first appearances in front of the camera were on Mister Rogers Neighborhood. He later burst onto the big screen in Ron Howard’s 1982 film Night Shift. Keaton went on to star in a host of comedic movies including Mr. Mom, Johnny Dangerously, and Gung Ho.

In 1988, Keaton was featured in the iconic horror-comedy Beetlejuice. Working with director Tim Burton on the film, Keaton clearly made an impression where Burton signed him to play the title role in 1989’s blockbuster Batman. While many panned the idea of Keaton as the caped crusader, the actor received critical accolades for his dark, brooding portrayal of Bruce Wayne, making the film a box office hit.

Keaton’s most acclaimed role was Riggan Thomson in Alejandro González Iñárritu’s 2014 film Birdman. The attention Keaton received put him back in the spotlight, earning him a Golden Globe award and Critics’ Choice Award, as well as nominations for an Oscar and a Screen Actors Guild Award.

Marriage and son/best friend

Keaton, who was born Michael Douglas, was married to actress Caroline McWilliams from 1982 to 1990. She passed away from cancer in 2010. Keaton commented on the loss of his ex-wife, praising her as a mother to their son Sean. “My sister and my brother both lost ex-spouses, and both said, ‘This is going to be harder than you think,'” Keaton told Elle in 2010. “And the feelings that came up were odd, but not in a bad way, necessarily, because we had remained close. She was a remarkable mom. Sean is the great guy he is because of her—we’ve always been tight, but now the bond’s even tighter. We’re the family now.”

The actor paid homage to his son in his 2015 Golden Globes speech upon receiving the Best Actor award. “My best friend is kind, intelligent, funny, talented, considerate, thoughtful,” he said on stage, according to the Daily Mail. “Did I say kind? He also happens to be my son, Sean.”

His son returned the adoration in his speech paying tribute to Keaton when he received a star on the Hollywood Walk of Fame in 2016. “I’ve seen everything from Batman to bath time when I was a young kid … but I’m so proud to be your son,” Sean said, according to the Pittsburgh Post-Gazette. “You’re my hero, my best friend, and I love you so much.”

90s couple

Keaton dated actress Courtney Cox of Friends fame from 1990 to 1995. In an interview with People at the time of their split, Cox said the decision to part ways was mutual.  “It’s the most important relationship I’ve ever had, and I think he’s the most wonderful person I’ve ever met,” she said of Keaton in November 1995. “We still love each other.”

Courteney Cox and Michael Keaton | Jeff Kravitz/FilmMagic, Inc.

The couple was known for being very private, rarely appearing together in public. Both being in show business, the two would often run lines with each other. “He always came up with the most clever ways of making a line funny,” Cox shared. “No matter how upset or pissed off I was, Michael could make a little face and crack me up.”

The actress revealed she wasn’t quite sure of what finally made them go their separate ways. “Nothing about our relationship was ever simple,” the former Friends star said.

Though the couple’s relationship did not succeed, they have both moved on and are currently thriving in their professional lives.