Suggestions by @user_26273

Valentino (Hazbin Hotel)

as The Corruptor in Sort by Tropes

Valentino (Hazbin Hotel)

as The Caligula in Sort by Tropes

Valentino (Hazbin Hotel)

as Bad Boss in Sort by Tropes

Valentino (Hazbin Hotel)

as Rape Is a Special Kind of Evil in Sort by Tropes

Troy Calypso

as Ambiguously Brown in Sort by Tropes

Tyreen Calypso

as Ambiguously Brown in Sort by Tropes

Dr. Jekyll/Mr. Hyde (Fredric March)

as The Best Classic Monsters in The Best Monsters of All Time

Emma Corrin

as X-Men in Hottest Actress by Franchise

Keisha Castle-Hughes

as Game of Thrones in Hottest Actress by Franchise

Alfre Woodard

as Star Trek in Hottest Actress by Franchise

Bridget Gregory

as The Corruptor in Sort by Tropes

Bridget Gregory

as Consummate Liar in Sort by Tropes

Bridget Gregory

as The Chessmaster in Sort by Tropes

Bridget Gregory

as The Beard in Sort by Tropes

Bridget Gregory

as Manipulative Bastard in Sort by Tropes

Bridget Gregory

as Femme Fatale in Sort by Tropes

Bridget Gregory

as For the Evulz in Sort by Tropes

Bridget Gregory

as Evil is Sexy in Sort by Tropes

Bridget Gregory

as Aloof Dark-Haired Girl in Sort by Tropes

Bridget Gregory

as Anti-Hero in Sort by Tropes