Suggestions by @saracuda

Warden Walker (Holes)

as Femme Fatalons in Sort by Tropes

Khal Drogo

as Emergency Transformation in Sort by Tropes

Harry Solomon (3rd Rock from the Sun)

as Eyes Always Shut in Sort by Tropes

Happy Hogan (MCU)

as The Driver in Sort by Tropes

Hawkeye

as Dramatic High Perching in Sort by Tropes

Milo Thatch

as Dork in a Sweater in Sort by Tropes

Arthur Read

as Dork in a Sweater in Sort by Tropes

Doug Funnie

as Dork in a Sweater in Sort by Tropes

Gentleman Jack

as Does Not Like Men in Sort by Tropes

Enid Hoopes (Legally Blonde)

as Does Not Like Men in Sort by Tropes

David Kidney (Legally Blonde)

as Dork in a Sweater in Sort by Tropes

The World Was Wide Enough (Hamilton)

as Death Song in Sort by Tropes

Adrian Monk

as Creature of Habit in Sort by Tropes

Margaret "Mags" Flanagan

as Cute Mute in Sort by Tropes

Jonathan Brown (Inspector Gadget)

as Crazy-Prepared in Sort by Tropes

FAKE

as Crazy-Prepared in Sort by Tropes

Ron Swanson

as Crazy-Prepared in Sort by Tropes

Chancellor Palpatine

as Corrupt Politician in Sort by Tropes

Harvey Dent

as Corrupt Politician in Sort by Tropes

Victoria Neuman

as Corrupt Politician in Sort by Tropes