The Saturday Night Live alum, 57, made a cameo appearance on The Fresh Prince of Bel-Air in 1995, playing Maurice, a famous actor, and Maurice’s sister, Jasmine. Rock was already a successful stand-up comedian at that point, but the Ali actor, 53, was just starting to become a household name.
Pinkett Smith, 50, also met her future husband on the set of Fresh Prince. In 1994, she auditioned to play Lisa Wilkes, the girlfriend of his character (also named Will Smith). The Magic Mike XXL actress lost the role to Nia Long, but she later gained a spouse — she and Smith tied the knot in December 1997. The couple went on to welcome son Jaden Smith, now 23, and daughter Willow Smith, now 21. (Will also shares son Trey, 29, with ex-wife Sheree Zampino.)
While Rock and the Men in Black star haven’t worked together since Fresh Prince, the Grown Ups actor and Pinkett Smith collaborated for the first time in 2005. The Matrix Reloaded star provided the voice of a hippo named Gloria in the animated film Madagascar, while Rock played a zebra named Marty. The twosome reprised their roles in the 2008 and 2012 sequels.
During the press tour for 2012’s Madagascar 3: Europe’s Most Wanted, Rock revealed that his children are big fans of Will and Pinkett Smith’s daughter, Willow. The Dogma star shares daughters Lola, 19, and Zahra, 17, with ex-wife Malaak Compton-Rock.
“Hey, my kids listen to your kids!” Rock said during an interview with Fuse at the time, recalling what he told his costar. “’21st Century Girl’ Oh, my God. And they love LMFAO, but they have no idea what it stands for.”
Four years later, however, tensions rose when Rock referenced the Smith family during his opening monologue while hosting the 2016 Oscars. The Academy faced criticism that year for a lack of diversity among the nominees.
“Jada got mad, said she’s not coming,” Rock said. “Jada boycotting the Oscars is like me boycotting Rihanna’s panties. I wasn’t invited.”
He went on to reference Will, who was snubbed that year for a nomination despite a critically acclaimed performance in the film Concussion. “It’s not fair that Will was this good and didn’t get nominated,” Rock quipped. “It’s also not fair that Will was paid $20 million for Wild Wild West.”
For a full history of Rock’s relationship with Will and Pinkett Smith, watch the video above.