Megan Fox, Holiday in the Sun (2001)
Megan Fox landed her first credited acting gig in 2001, when she starred alongside the Olsen twins in their direct-to-video Holiday in the Sun. One year before she joined Ocean Avenue and three before she made her big-screen debut, Fox played Brianna Wallace, a snobby rich girl who faces off against Ashley’s character, Alex, for the heart of the Atlantis Resort’s resident dreamboat employee, Jordan.
Michael Cera, Switching Goals (1999)
Eight years before Juno and Superbad, Michael Cera was a kid named Taylor in the 1999 Mary-Kate and Ashley movie Switching Goals. The future Arrested Development star appeared as a very particular young man with plans to try out for the soccer team.
Cloris Leachman, Double Double Toil and Trouble (1993)
Cloris Leachman brought her Oscar-winning acting chops to the Olsen twins universe in 1993, appearing alongside the child stars in Double Double Toil and Trouble. The Mary Tyler Moore Show alum played Aunt Agatha, the twins’ intimidating great-aunt.
Jesse Spencer, Winning London (2001)
Years before he became House‘s Dr. Robert Chase or Chicago Fire‘s Matthew Casey, Jesse Spencer was Winning London‘s Lord James Browning Jr. The Australian actor played a British nobleman who starts a relationship with Mary-Kate’s character, Chloe.
Steve Guttenberg and Kirstie Alley, It Takes Two (1995)
Police Academy‘s Steve Guttenberg and Cheers‘ Kirstie Alley teamed up in 1995 for Mary-Kate and Ashley’s It Takes Two. The stars played Roger Callaway and Diane Barrows, a camp owner and social worker, who fall in love thanks to some hijinks from Mary-Kate and Ashley’s Amanda Lemmon and Alyssa Callaway.
Eric McCormack, Double Double Toil and Trouble (1993)
Five years before Will and Grace hit screens, Eric McCormack was playing Don in 1993’s Double Double Toil and Trouble. The future Emmy winner joined the Olsen twins’ movie as their father.
Troian Bellisario, Billboard Dad (1998)
Fans may know Troian Bellisario best as Pretty Little Liars‘ Spencer Hastings, but the actress landed one of her first acting roles in 1998 with Billboard Dad. Bellisario starred alongside Mary-Kate and Ashley as Kristen, a girl the twins hang out with at the pool.
Jared Padalecki, New York Minute (2004)
Rhea Perlman, To Grandmother’s House We Go (1992)
Mary-Kate and Ashley appeared alongside another Cheers star in 1992, when Rhea Perlman joined To Grandmother’s House We Go. She played a robber named Shirley.
Austin Nichols, Holiday in the Sun (2001)
The Walking Dead‘s Austin Nichols had a slightly sunnier turn alongside Mary-Kate and Ashley more than a decade before he played Spencer Monroe. Nicholas appeared as Mary-Kate’s love interest Griffen in 2001’s Holiday in the Sun.