Suggestions by @amyhoward

Dove Cameron

as Benny Hanson in Pretty in Pink

Score: +2

Evil Giselle

as Wicked Stepparent in Sort by Tropes

Score: +3

Kol Mikaelson

as Wicked Stepparent in Sort by Tropes

Score: +3

Regina Mills

as Wicked Witch in Sort by Tropes

Score: +3

Adagio Dazzle

as Queen Bee in Sort by Tropes

Score: +7

Unique Adams

as Ambiguous Gender in Sort by Tropes

Score: +3

Sherri "Cherry" Valance

as All Girls Want Bad Boys in Sort by Tropes

Score: +6

Betty Rizzo

as All Girls Want Bad Boys in Sort by Tropes

Score: +7

Rosie Gonzalez

as Adopted into Royalty in Sort by Tropes

Score: +1

Artie Abrams

as Adorkable in Sort by Tropes

Score: +4

Nina Dobrev

as Princess Adana/The Beast in Beauty and the Beast 2017 (Genderbend)

Score: +1

Nathaniel Buzolic

as Ben in Beauty and the Beast 2017 (Genderbend)

Score: +2

Darren Criss

as Esmeralda in Female Disney Characters (Genderswap)

Score: 0

Ross Lynch

as Tinkerbell in Female Disney Characters (Genderswap)

Score: +2

Margaret Hamilton

as Elphaba in Ozma of Oz (1941)

Score: +1

Daisy Ridley

as Rey in Kylo: A Star Wars Story

Score: +2

Zendaya

as Lea Edwards in Mean Girls (2019)

Score: +1

Karan Brar

as Kevin Gnapoor in Mean Girls (2019)

Score: +1

Dianna Agron

as Regina George in Mean Girls (2019)

Score: 0

Hart Denton

as Damian Leigh in Mean Girls (2019)

Score: 0