Suggestions by @masterofcool

Fairuza Balk

as Hilda in Hilda (1980s)

Mark Hamill

as Ferris Bueller in Ferris Bueller's Day Off (1976)

Carrie Fisher

as Sloane Peterson in Ferris Bueller's Day Off (1976)

Imelda Staunton

as Felicia Alden in The Witches of Eastwick (1997)

Geena Davis

as Alexandra Medford in The Witches of Eastwick (1997)

Kelly Ripa

as Kelly Ripa in Cheaper by the Dozen (1998)

Regis Philbin

as Regis Philbin in Cheaper by the Dozen (1998)

Henry Thomas

as Bill Denbrough in It (1980's)

Christopher Plummer

as Martin Brenner in Stranger Things 1991

Patrick Dempsey

as Miles in Project X (1992)

Mark Wahlberg

as Marty Mcfly in Back to the future (1995)

Carrie Fisher

as Jane Spofford in The Witches of Eastwick (1997)

Naomi Watts

as Sukie Ridgemont in The Witches of Eastwick (1997)

James Woods

as Daryl Van Horne in The Witches of Eastwick (1997)

Corey Feldman

as Dax in Project X (1992)

Jerry O'Connell

as J.B. in Project X (1992)

Christopher Lloyd

as T-Rick in Project X (1992)

Gwyneth Paltrow

as Kirby Griffin in Project X (1992)

Kirk Cameron

as Roger Costa in Project X (1992)

Wil Wheaton

as Thomas Kub in Project X (1992)