Suggestions by @jasleenfaydelarosa

Jane Fonda

as Rosie Dickson in Dumplin (1988)

Denzel Washington

as Kalvin Summers in Beacon Street Boys ('70s Genderswap)

William Katt

as Charlie Ramsey in Beacon Street Boys ('70s Genderswap)

Henry Fonda

as Bobby Rydell in 60s Actors as Adults

Walter Matthau

as Robert De Niro in 60s Actors as Adults

Jack Lemmon

as Martin Sheen in 60s Actors as Adults

Jack Lemmon

as The Creature in Lisa Frankenstein (60s Adult Cast)

Astrid Deetz

as Jenna Ortega in Ranking Characters By Actor

Miyoshi Umeki

as Taffy Swallows in Lisa Frankenstein (60s Adult Cast)

Miyoshi Umeki

as Nancy Kwan in 60s Actors as Adults

Lee Remick

as Lisa Swallows in Lisa Frankenstein (60s Adult Cast)

Lee Remick

as Joan Van Ark in 60s Actors as Adults

Nichelle Nichols

as Tricia in Lisa Frankenstein (60s Adult Cast)

Tippi Hedren

as Lori in Lisa Frankenstein (60s Adult Cast)

Anne Bancroft

as Lesley Ann Warren in 60s Actors as Adults

Lesley Ann Warren

as Abby Stevenson in The Babysitters Club ('60s Live Action)

Christopher Walken

as Logan Bruno in The Babysitters Club ('60s Live Action)

Goldie Hawn

as Shannon Kilbourne in The Babysitters Club ('60s Live Action)

Patty Duke

as Dawn Schafer in The Babysitters Club ('60s Live Action)

Annette Funicello

as Mary Anne Spier in The Babysitters Club ('60s Live Action)