Suggestions by @jharmony

Uncle Dan (Migration)

as Uncle Dan in Migration (Crossover)

Dennis Quaid

as Grandmamah in Ruby Gillman: Teenage Kraken (Genderswap)

Angelina Jolie

as Nerrisa in Ruby Gillman Teenage Kraken Live Action

Brandy Norwood

as Meridian Clade in Strange World (Live-Action)

Roman Banks

as Connor in Ruby Gillman Teenage Kraken Live Action

Milo Manheim

as Trevin in Ruby Gillman Teenage Kraken Live Action

Auli'i Cravalho

as Bliss in Ruby Gillman Teenage Kraken Live Action

David Harbour

as Arthur in Ruby Gillman Teenage Kraken Live Action

Jenna Rink

as '80s Hair in Sort by Tropes

Hole-N'-Fun (Trolls Band Together)

as Abandoned Area in Sort by Tropes

Honey Lemon

as Viva in Trolls Band Together (But with different characters)

Meesha Garbett

as Veruca Salt in Willy Wonka and The Chocolate Factory

Jack Dylan Grazer

as Dylan West in Zoom: Academy For Superheroes (Remake)

Joshua Bassett

as Dylan West in Zoom: Academy For Superheroes (Remake)

Meg Donnelly

as Summer Jones in Zoom: Academy For Superheroes (Remake)

Storm Reid

as Summer Jones in Zoom: Academy For Superheroes (Remake)

Madison Skye Validum

as Cindy Collins in Zoom: Academy For Superheroes (Remake)

Dwayne Johnson

as Zoom/Jack in Zoom: Academy For Superheroes (Remake)

Storm Reid

as The Princess in Actors You'd like to see in a Medieval/Fantasy Movie

*NSYNC

as Famous Rock Band at prom in Typical Teen Movie/Television Series