Adam Sandler (as Billy Madison) with Bridgette Wilson (as Veronica Vaughn)
in Billy Madison (1995)

Adam Sandler (as Happy Gilmore) with Julie Bowen (as Virginia Venit)
in Happy Gilmore (1996)

Adam Sandler (as Robbie) with Drew Barrymore (as Julia)
in The Wedding Singer (1998)

Adam Sandler (as Robert 'Bobby' Boucher Jr.) with Fairuza Balk (as Vicki Vallencourt)
in The Waterboy (1998)

Adam Sandler (as Sonny Koufax) with Kristy Swanson (as Vanessa)
in Big Daddy (1999)

Adam Sandler (as Sonny Koufax) with Joey Adams (as Layla Maloney)
in Big Daddy (1999)

Adam Sandler (as Nicky) with Patricia Arquette (as Valerie Veran)
in Little Nicky (2000)

Adam Sandler (as Barry Egan) with Emily Watson (as Lena Leonard)
in Punch-Drunk Love (2002)

Adam Sandler (as Longfellow Deeds) with Winona Ryder (as Babe Bennett)
in Mr. Deeds (2002)

Adam Sandler (as Dave Buznik) with Marisa Tomei (as Linda)
in Anger Management (2003)

Adam Sandler (as Henry Roth) with Drew Barrymore (as Lucy Whitmore)
in 50 First Dates (2004)

Adam Sandler (as John Clasky) with Tea Leoni (as Deborah Clasky)
in Spanglish (2004)

Adam Sandler (as John Clasky) with Paz Vega (as Flor Moreno)
in Spanglish (2004)

Adam Sandler (as Michael Newman) with Kate Beckinsale (as Donna Newman)
in Click (2006)

Adam Sandler (as Chuck Levine) with Jessica Biel (as Alex McDonough)
in I Now Pronounce You Chuck & Larry (2007)

Adam Sandler with Emmanuelle Chriqui (as Dalia)
in You Don`t Mess with the Zohan (2008)

Adam Sandler with Salma Hayek
in Grown Ups (2010)

Who's Dated Who content is contributed and edited by our readers. Please report errors or omissions on this page.