Suggestions by @elisep

Roman Griffin Davis

as Little red ridinghood in Into The Woods Genderswap

Score: +1

Derek Klena

as Baker’s Wife in Into The Woods Genderswap

Score: +1

Neil Patrick Harris

as Jack’s mother in Into The Woods Genderswap

Score: +1

Christy Altomare

as Baker in Into The Woods Genderswap

Score: +1

James Tolbert

as The Balladeer in Assassins

Score: 0

Colton Ryan

as John Hinckley, Jr. in Assassins

Score: +1

Isaac Powell

as Leon Czolgosz in Assassins

Score: +1

Christian Borle

as Charles Guiteau in Assassins

Score: +1

Grace McLean

as Sara Jane Moore in Assassins

Score: +1

Ramin Karimloo

as John Wilkes Booth in Assassins

Score: +1

Andy Karl

as Samuel Byck in Assassins

Score: +1

John Gallagher Jr.

as The Balladeer in Assassins

Score: 0