546 suggestions

Leslie Uggams
as Marquis de Lafayette/Thomas Jefferson in Hamilton (1980s) Genderbend
Gary Burghoff
as Lord Savage in Jekyll and Hyde Musical (Genderswap)

Keegan-Michael Key
as Evil DJ in Zoolander

Lolly Adefope
as Katinka in Zoolander

Richard Ayoade
as J.P Prewett in Zoolander

Tim Meadows
as J.P Prewett in Zoolander

Cher (Cheryl Sarkisian)
as George Washington in Hamilton (1980s) Genderbend
Nicholas Christopher
as Angelica Schuyler Church in Hamilton (genderbent)
Nicholas Christopher
as Princess Mary Bolkonskaya in Natasha, Pierre, and The Great Comet of 1812 (Genderbend)

Will Roland
as Aeolus in Epic: The Musical (Genderbent)

The Hunchback of Notre Dame (1996 film)
as Animation Inspo. (and also Cinematography) in Natasha, Pierre, and The Great Comet of 1812 (Genderbend)

The Prince of Egypt
as Animation Inspo. (and also Cinematography) in Natasha, Pierre, and The Great Comet of 1812 (Genderbend)

Daisies (1966)
as Animation Inspo. (and also Cinematography) in Natasha, Pierre, and The Great Comet of 1812 (Genderbend)

Amadeus (film)
as Animation Inspo. (and also Cinematography) in Natasha, Pierre, and The Great Comet of 1812 (Genderbend)

Howl's Moving Castle
as Animation Inspo. (and also Cinematography) in Natasha, Pierre, and The Great Comet of 1812 (Genderbend)

Treasure Planet
as Animation Inspo. (and also Cinematography) in Natasha, Pierre, and The Great Comet of 1812 (Genderbend)

Moulin Rouge!
as Animation Inspo. (and also Cinematography) in Natasha, Pierre, and The Great Comet of 1812 (Genderbend)

Andrea Macasaet
as Fedya Dolokhov in Natasha, Pierre, and The Great Comet of 1812 (Genderbend)

Adam Driver
as Marya Dmitriyevna Akhrosimova in Natasha, Pierre, and The Great Comet of 1812 (Genderbend)

Ariana Grande
as Anatole Kuragin in Natasha, Pierre, and The Great Comet of 1812 (Genderbend)