Suggestions by @kirstentoth

Keegan-Michael Key

as Principal Ron Duvall in Mean Girls (2024)

Debbie Reynolds

as Beca Mitchell in Pitch Perfect in the Golden Age of Hollywood

Danny Kaye

as Bumper Allen in Pitch Perfect in the Golden Age of Hollywood

Cary Grant

as John Smith in Pitch Perfect in the Golden Age of Hollywood

Lucille Ball

as Gail Abernathy-McKadden-Feinberger in Pitch Perfect in the Golden Age of Hollywood

Rosalind Russell

as Gail Abernathy-McKadden-Feinberger in Pitch Perfect in the Golden Age of Hollywood

Marilyn Monroe

as Stacie Conrad in Pitch Perfect in the Golden Age of Hollywood

Lena Horne

as Cynthia-Rose Adams in Pitch Perfect in the Golden Age of Hollywood

Mickey Rooney

as Benji Applebaum in Pitch Perfect in the Golden Age of Hollywood

Grace Kelly

as Aubrey Posen in Pitch Perfect in the Golden Age of Hollywood

Gene Kelly

as Jesse Swanson in Pitch Perfect in the Golden Age of Hollywood

Doris Day

as Chloe Beale in Pitch Perfect in the Golden Age of Hollywood

Ethel Merman

as Patricia "Fat Amy" Hobart in Pitch Perfect in the Golden Age of Hollywood

Audrey Hepburn

as Beca Mitchell in Pitch Perfect in the Golden Age of Hollywood