Suggestions by @timemachine

Winona Ryder

as Princess Bubblegum in Adventure Time ('80s Live Action)

Anthony Michael Hall

as Finn Mertens in Adventure Time ('80s Live Action)

Christine Cavanaugh

as Stretchette (voice) in Casper (1995 Genderswap)

Tress MacNeille

as Stinkette (voice) in Casper (1995 Genderswap)

Kathy Najimy

as Fatsa (voice) in Casper (1995 Genderswap)

Rosie O'Donnell

as Fatsa (voice) in Casper (1995 Genderswap)

Brooke Shields

as Dr. Jasmine Harvey in Casper (1995 Genderswap)

Matthew Lawrence

as Keith Harvey in Casper (1995 Genderswap)

Ariana Richards

as Human Cassie in Casper (1995 Genderswap)

Anndi McAfee

as Cassie McFadden (voice) in Casper (1995 Genderswap)

Steven Spielberg

as Director in Code Lyoko ('80s Live Action)

Steven Spielberg

as Director in The Secret Saturdays ('80s Live Action)

Kate Capshaw

as Drew Saturday in The Secret Saturdays ('80s Live Action)

Tina Yothers

as Doris Zander in Ouija ('80s)

Olivia D'Abo

as Debbie Galardi in Ouija ('80s)

Crispin Glover

as Pete in Ouija ('80s)

Anthony Kramreither Jr.

as Trevor in Ouija ('80s)

Renee Murphy

as Isabelle in Ouija ('80s)

Winona Ryder

as Sarah Morris in Ouija ('80s)

Diane Lane

as Laine Morris in Ouija ('80s)