Suggestions by @krmickey97

Brooke Shields

as Taylor Vaughan in She's All That (1984)

Johnny Depp

as Zach Siler in She's All That (1984)

Emilio Estevez

as Zach Siler in She's All That (1984)

Michael Schoeffling

as Zach Siler in She's All That (1984)

Sarah Jessica Parker

as Laney Boggs in She's All That (1984)

Courteney Cox

as Laney Boggs in She's All That (1984)

Jami Gertz

as Laney Boggs in She's All That (1984)

Jeff Cohen

as Gibby in iCarly (1987-(1992)

Devin Ratray

as Gibby in iCarly (1987-(1992)

Steve Buscemi

as Spencer Shay in iCarly (1987-(1992)

John Stamos

as Spencer Shay in iCarly (1987-(1992)

Bruce Campbell

as Spencer Shay in iCarly (1987-(1992)

Wil Wheaton

as Freddie Benson in iCarly (1987-(1992)

Sean Astin

as Freddie Benson in iCarly (1987-(1992)

Christian Bale

as Freddie Benson in iCarly (1987-(1992)

Corey Feldman

as Freddie Benson in iCarly (1987-(1992)

Ben Affleck

as Freddie Benson in iCarly (1987-(1992)

Christina Applegate

as Sam Puckett in iCarly (1987-(1992)

Heather Graham

as Sam Puckett in iCarly (1987-(1992)

Alyssa Milano

as Carly Shay in iCarly (1987-(1992)