Suggestions by @chris83

Zach Gilford

as Dennis Guilder in Christine (2003)

Zach Gilford

as Larry Granger in Fear Street: Prom King (2005 Genderswap)

Zach Gilford

as Matt Trent in Clown in a Cornfield (2005)

Zach Gilford

as Jimmy in Fear Street: Prom Queen (2005)

Zach Gilford

as Andy Bradshaw in D.A.N.S (D.E.B.S. 2004 Genderswap)

Zach Gilford

as Scott Reed in 13 Reasons Why (2002-2005)

Zach Gilford

as Charlie St. George in 13 Reasons Why (2002-2005)

Zach Gilford

as Dean Di Laurentis in Off Campus (2006-)

Zach Gilford

as Samuel "Sam" Montgomery in A Cinderfella Story (2004 Genderswap)

Zach Gilford

as Kyle in Modern Guys (Modern Girls 2006 Genderswap)

Zach Gilford

as Charlie "Chugs" Bradley in Fraternity Row (Sorority Row 2004 Genderswap)

Zach Gilford

as Kevin Presley in Black Christmas (2006 Genderswap)

Samaire Armstrong

as Jules Logan in Off Campus (2006-)

Annette Bening

as Francine Atwood in The OC (2003-2007) (genderswap)

Rosanna Arquette

as Francine Atwood in The OC (2003-2007) (genderswap)

Linda Blair

as Francine Atwood in The OC (2003-2007) (genderswap)

Linda Hamilton

as Francine Atwood in The OC (2003-2007) (genderswap)

Heather Locklear

as Francine Atwood in The OC (2003-2007) (genderswap)

Eileen Davidson

as Francine Atwood in The OC (2003-2007) (genderswap)

Sharon Stone

as Francine Atwood in The OC (2003-2007) (genderswap)