Suggestions by @timemachine

Jared Leto

as Oliver Schermerhorn in Everything Sucks! ('90s)

Jonathan Taylor Thomas

as Tyler Bowen in Everything Sucks! ('90s)

Nia Long

as Sherry O'Neil in Everything Sucks! ('90s)

Jim Carrey

as Ken Messner in Everything Sucks! ('90s)

Christina Ricci

as Kate Messner in Everything Sucks! ('90s)

Ray J

as Luke O'Neil in Everything Sucks! ('90s)

Heath Ledger

as Billy Hargrove in Stranger Things ('90s)

Robin Williams

as Jim Hopper in Stranger Things ('90s)

Drew Barrymore

as Robin Buckley in Stranger Things ('90s)

River Phoenix

as Jonathan Byers in Stranger Things ('90s)

Linda Cardellini

as Nancy Wheeler in Stranger Things ('90s)

Ashton Kutcher

as Steve Harrington in Stranger Things ('90s)

Lindsay Lohan

as Max Mayfield in Stranger Things ('90s)

Ben Savage

as Dustin Henderson in Stranger Things ('90s)

Lee Thompson Young

as Lucas Sinclair in Stranger Things ('90s)

Matthew Lawrence

as Will Byers in Stranger Things ('90s)

Bradley Pierce

as Mike Wheeler in Stranger Things ('90s)

Christina Ricci

as Eleven in Stranger Things ('90s)

Ralph Macchio

as Chase Hammond in Drive Me Crazy (1984)

Heather Locklear

as Nicole Maris in Drive Me Crazy (1984)