Leslie Mann & Judd Apatow – Married Since 1997

Although dating websites were already a thing in the ’90s, actress Leslie Mann and director Judd Apatow met the old-fashioned way… at least in Hollywood. As the story goes, they met while Mann was auditioning for a role in “The Cable Guy,” and Apatow jokingly declared her the future Mrs. Apatow.

Well, he was clearly onto something because she indeed got that title when they wed each other in 1997. Since then, the couple has collaborated several times on both films and their two daughters. They worked together once again for the 2022 film “The Bubble.”