Simon Helberg
Baron Vladimir Harkonin
Barron Trump
Ginger Grant
Dolly Parton
Popeye?
Gilbert Gottfried
Holly Gennaro (Maclane)
Vivian Vance
Ida Morgenstern (Rhoda’s mother)?
Shirley Jones
Prof. Harold Hill?
Bobcat Goldthwaite
George Jefferson?
Kareem Abdul-Jabar
Lou Grant?
n/m
Jimmy Stewart
Amy Fowler Kane (in High Noon)
Fran Drescher
Dr. Strangelove
Peter Fonda
Buzz Lightyear
Gary Shandling
Mona Robinson
Kathleen Freeman
Oliver Wendell Douglas?
George Sanders
The Sundance Kid
Chris Farley
Fast Eddie Felson?
Jerry Lewis
King Kong?
Wally Cox
Sophia Petrillo
Colin Firth
I’d initially thought David Tennat but he might be able to pull it. Firth is more of a Dorothy, and I say this having seen both in drag.
Ethan Hunt
Flip Wilson
Martin Crane (Frasier’s dad)?