Suggestions by @ghtyfsh
24 suggestions
Phillipa Soo
as Marian Paroo in Music Man

Tom Holland
as James Dean in Old Hollywood actors
Marilyn Monroe
as Favorite Movie Actress in MyCast Choice Awards

Cary Grant
as Favorite Movie Actor in MyCast Choice Awards
James Stewart
as Favorite Movie Actor in MyCast Choice Awards

Grace Kelly
as Favorite Movie Actress in MyCast Choice Awards
Audrey Hepburn
as Favorite Movie Actress in MyCast Choice Awards
Lucille Ball
as Favorite Comedian in MyCast Choice Awards
Frank Sinatra
as Favorite Male Musician in MyCast Choice Awards
Groucho Marx
as Favorite Comedian in MyCast Choice Awards
Harpo Marx
as Favorite Comedian in MyCast Choice Awards
Donald O'Connor
as Favorite Deceased Celebrity (Male) in MyCast Choice Awards
Robert Downey Jr.
as Harold Hill in Music Man

Ginger Rogers
as G in Best Actor starting with every letter
Donald O'Connor
as D in Best Actor starting with every letter

Grace Kelly
as Actresses in Best Actors Of All Time
Dick Van Dyke
as Dancers in Face Claims Sorted by Professions
Donald O'Connor
as Dancers in Face Claims Sorted by Professions

Ginger Rogers
as Dancers in Face Claims Sorted by Professions
Groucho Marx
as Comedians in Best Actors Of All Time