Suggestions by @timemachine

Ann-Margret

as Alicia Silverstone in '90s Actors in the '60s

Robert De Niro

as '60s in Which Actor Should've Played Nick Castle in Various Decades

Milo Manheim

as 2020s in Which Actor Should've Played Nick Castle in Various Decades

Dylan Minnette

as 2010s in Which Actor Should've Played Nick Castle in Various Decades

Justin Long

as 2000s in Which Actor Should've Played Nick Castle in Various Decades

Jared Leto

as '90s in Which Actor Should've Played Nick Castle in Various Decades

Keanu Reeves

as '80s in Which Actor Should've Played Nick Castle in Various Decades

John Travolta

as '70s in Which Actor Should've Played Nick Castle in Various Decades

Jessica Belkin

as 2020s in Which Actress Should've Played Elizabeth Williams in Various Decades

Madison Iseman

as 2010s in Which Actress Should've Played Elizabeth Williams in Various Decades

Laura Vandervoort

as 2000s in Which Actress Should've Played Elizabeth Williams in Various Decades

Alicia Silverstone

as '90s in Which Actress Should've Played Elizabeth Williams in Various Decades

Olivia D'Abo

as '80s in Which Actress Should've Played Elizabeth Williams in Various Decades

Linda Purl

as '70s in Which Actress Should've Played Elizabeth Williams in Various Decades

Joan Van Ark

as '60s in Which Actress Should've Played Elizabeth Williams in Various Decades

Malese Jow

as Lee Lee in Dexter's Laboratory (2000s live-action movie)

Devon Werkheiser

as Douglas E. Mordecai III in Dexter's Laboratory (2000s live-action movie)

Jantrice

as John Cho in Which Character Should Actors Have Played Genderswapped in the '90s

Gwen Wu

as John Cho in Which Character Should Actors Have Played Genderswapped in the '90s

Anissa Chen (Carrie 2013)

as John Cho in Which Character Should Actors Have Played Genderswapped in the '90s