Suggestions by @daredevilagain22

Sarah Michelle Gellar

as 2000s in What Actresses Could've Played Heather Chandler Various Decades?

Rose McGowan

as 2000s in What Actresses Could've Played Heather Chandler Various Decades?

Fairuza Balk

as Jade West in Victorious (90s)

Costas Mandylor

as Roberto in Monster

Elizabeth Gillies

as Courtney Shayne in Jawbreaker Remake

Elle Fanning

as Cher Horowitz in Clueless

Jenny Boyd

as Kirari Momobami in Kakegurui (Live Action Series)

Jenny Boyd

as Esdeath in Akame Ga Kill (Live Action)

Costas Mandylor

as Roberto in Monster

Paul Wesley

as Prince Hans in Disney Villains

Michael C. Hall

as Sousuke Aizen in Bleach

Samara Weaving

as Junko Enoshima in Danganronpa

Bella Thorne

as Junko Enoshima in Danganronpa

Madeline Petsch

as Junko Enoshima in Danganronpa