Suggestions by @jasleenfaydelarosa

Ricki Lake

as Becca Hanscom in It (80's Teen Cast Genderswap)

Andrew McCarthy

as Stan Uris in It (80s Teen Cast)

Matthew Broderick

as Eddie Kaspbrak in It (80s Teen Cast)

Kiefer Sutherland

as Henry Bowers in It (80s Teen Cast)

Blair Underwood

as Mike Hanlon in It (80s Teen Cast)

Molly Ringwald

as Beverly Marsh in It (80s Teen Cast)

Dan Schneider

as Ben Hanscom in It (80s Teen Cast)

Marta Cabrera (Knives Out)

as Jessica Alba in Which characters should actors have played in the 90's?

Marta Cabrera (Knives Out)

as Salma Hayek in Which characters should actors have played in the 80’s?

Anthony Kramreither Jr.

as Prince Domenico Da Silvano in Monte Carlo (80s)

Emilio Estevez

as Riley in Monte Carlo (80s)

Whoopi Goldberg

as Kelley Summers in Beacon Street Girls (80s Adult Cast)

Tom Cruise

as Brian Montgomery in A Cinderella Story (80s Genderswap)

Eric Stoltz

as Colin in A Cinderella Story (80s Genderswap)

Blair Underwood

as Mason in A Cinderella Story (80s Genderswap)

Katherine Kamhi

as Davina in A Cinderella Story (80s Genderswap)

Samantha Langevin

as Harriet Montgomery in A Cinderella Story (80s Genderswap)

William Zabka

as Shaun Cunmings in A Cinderella Story (80s Genderswap)

Bea (Anyone but You)

as Olivia D'Abo in Which characters should actors have played in the 80’s?

Winona Ryder

as Carrie Farrell in A Cinderella Story (80s Genderswap)