Suggestions by @pumpkinroll

Taylor Swift

as Ozzy in Helluva Boss gender swapped

Score: +1

Harry Styles

as Beelzebub in Helluva Boss gender swapped

Score: +1

Alano Miller

as Mr. Heron in Mean Girls the musical movie

Score: +1

Brett Dier

as Mr. Duvall in Mean Girls the musical movie

Score: +1

Philipa Soo

as Mrs. Heron in Mean Girls the musical movie

Score: +1

Ginnifer Goodwin

as Mrs. Heron in Mean Girls the musical movie

Score: +1

Emilie de Ravin

as Ms. Norbury in Mean Girls the musical movie

Score: +3

Jennifer Morrison

as Ms. Norbury in Mean Girls the musical movie

Score: +1

Dove Cameron

as Regina George in Mean Girls the musical movie

Score: +2

Keala Settle

as Martha Dunnstock in Heather's

Score: +1

Presley Ryan

as Heather Duke in Heather's

Score: +1

Presley Ryan

as Heather McNamara in Heather's

Score: +1

Margot Robbie

as Heather Chandler in Heather's

Score: +1

Barret Wilbert Weed

as Janis in Mean Girls the musical movie

Score: +2

Nick Jonas

as Aaron Samuels in Mean Girls the musical movie

Score: 0

Ethan Slater

as Damien in Mean Girls the musical movie

Score: +1

Kristin Chenoweth

as Mrs. George in Mean Girls the musical movie

Score: +2

Mackenzie Ziegler

as Karen Smith in Mean Girls the musical movie

Score: +1

Marissa Bode

as Gretchen Weiners in Mean Girls the musical movie

Score: +2

Sophia Anne Caruso

as Regina George in Mean Girls the musical movie

Score: 0