Suggestions by @victoriasouza

Nathan Lane

as Mother Abbess in The Sound of Music (Genderswap)

Patrick Page

as Mother Abbess in The Sound of Music (Genderswap)

Tilda Swinton

as Baron von Trapp in The Sound of Music (Genderswap)

Hannah Waddingham

as Baron von Trapp in The Sound of Music (Genderswap)

Charlize Theron

as Baron von Trapp in The Sound of Music (Genderswap)

Cate Blanchett

as Baron von Trapp in The Sound of Music (Genderswap)

Andrew Garfield

as Maria Von Trapp in The Sound of Music (Genderswap)

Ben Platt

as Maria Von Trapp in The Sound of Music (Genderswap)

Jonathan Groff

as Maria Von Trapp in The Sound of Music (Genderswap)

Jonathan Groff

as Zoe Trent in Littlest Pet Shop Advanced Casting :(Genderswap)

Sacha Baron Cohen

as Sunil Nelva in Littlest Pet Shop (Advanced Casting)

Lady Gaga

as Zoe Trent in Littlest Pet Shop (Advanced Casting)

Eric Bauza

as Diane in Hoppers (Genderswap)

Anthony Warlow

as Miss Agatha Hannigan in Annie (Genderswap)

James Corden

as Lily St. Regis in Annie (Genderswap)

Derek Hough

as Lily St. Regis in Annie (Genderswap)

Billy Magnussen

as Lily St. Regis in Annie (Genderswap)

Chord Overstreet

as Lily St. Regis in Annie (Genderswap)

Freddie Stroma

as Lily St. Regis in Annie (Genderswap)

Drew Van Acker

as Lily St. Regis in Annie (Genderswap)