Suggestions by @lump0324

Stephen Sondheim

as Composer in Gypsy (2004)

Steven Spielberg

as Director in Gypsy (2004)

Andrew Rannells

as Yonkers in Gypsy (2004)

Rory O'Malley

as L.A. in Gypsy (2004)

Gavin Creel

as Tulsa in Gypsy (2004)

Idina Menzel

as Tessie Tura in Gypsy (2004)

Kristin Chenoweth

as Miss Electra in Gypsy (2004)

Renée Elise Goldsberry

as Miss Mazeppa in Gypsy (2004)

Sutton Foster

as Tessie Tura in Gypsy (2004)

Kevin Kline

as Herbie Sommers in Gypsy (2004)

Annaleigh Ashford

as June Havoc in Gypsy (2004)

Anne Hathaway

as Louise Hovick in Gypsy (2004)

Glenn Close

as Rose Hovick in Gypsy (2004)

Bette Midler

as Rose Hovick in Gypsy (2004)

Liza Minnelli

as Rose Hovick in Gypsy (2004)

Liza Minnelli

as Mama Rose in Gypsy (2004)

Meryl Streep

as Mama Rose in Gypsy (2004)

Glenn Close

as Mama Rose in Gypsy (2004)

Bette Midler

as Mama Rose in Gypsy (2004)

Alma Deutscher

as Composer in The Sound of Music