Suggestions by @andymayer

Negan Smith

as Jeffrey Dean Morgan in Define Perfect Casting

Janet van Dyne (Marvel Cinematic Universe)

as Michelle Pfeiffer in Define Perfect Casting

Huntress (DC Extended Universe)

as Mary Elizabeth Winstead in Define Perfect Casting

Ozymandias

as Jeremy Irons in Define Perfect Casting

Owlman (DC)

as James Woods in Define Perfect Casting

Gloomius Maximus

as James Woods in Define Perfect Casting

Dr. Phillium Benedict

as James Woods in Define Perfect Casting

Seth Brundle

as Jeff Goldblum in Define Perfect Casting

The Wizard of Oz (Wicked)

as Jeff Goldblum in Define Perfect Casting

The Grandmaster (Marvel Cinematic Universe)

as Jeff Goldblum in Define Perfect Casting

Eda Clawthorne

as Wendie Malick in Define Perfect Casting

Sir Malachi

as Paul Reubens in Define Perfect Casting

Walt Disney

as Tom Hanks in Define Perfect Casting

Magneto (X-Men Legends)

as Tony Jay in Define Perfect Casting

Chairface Chippendale

as Tony Jay in Define Perfect Casting

Galactus

as Tony Jay in Define Perfect Casting

Dr. Lipschitz (Rugrats)

as Tony Jay in Define Perfect Casting

Lickboot

as Tony Jay in Define Perfect Casting

Wraith

as Tony Jay in Define Perfect Casting

Megabyte

as Tony Jay in Define Perfect Casting