Suggestions by @timemachine

Nichelle Nichols

as Sheri Holland in 13 Reasons Why (1967)

Diahann Carroll

as Jessica Davis in 13 Reasons Why (1967)

Cher

as Skye Miller in 13 Reasons Why (1967)

Michelle Phillips

as Chlöe Rice in 13 Reasons Why (1967)

Sally Field

as Hannah Baker in 13 Reasons Why (1967)

Dustin Hoffman

as Clay Jensen in 13 Reasons Why (1967)

Jane Fonda

as Karen Smith in Mean Girls (1964)

Sally Field

as Gretchen Weiners in Mean Girls (1964)

Ann-Margret

as Regina George in Mean Girls (1964)

Nichelle Nichols

as Dionne Davenport in Clueless (1965)

Ann-Margret

as Cher Horowitz in Clueless (1965)

Isabel May

as Lynda van der Klok in Halloween (2027)

Audrey Grace Marshall

as Laurie Strode in Halloween (2027)

Teagan Croft

as Judith Myers in Halloween (2027)

Edward Furlong

as Kevin Levin in Ben 10 (early '90s)

Christina Ricci

as Gwen Tennyson in Ben 10 (early '90s)

Macaulay Culkin

as Ben Tennyson in Ben 10 (early '90s)

Katherine Heigl

as Jade Butterfield in Endless Love ('90s)

Mena Suvari

as Jade Butterfield in Endless Love ('90s)

Rachel Blanchard

as Jade Butterfield in Endless Love ('90s)