Suggestions by @kamsismith

James Dean

as 1950s in What Actors Could've Played Man with No Name in Various Decades?

Humphrey Bogart

as 1940s in What Actors Could've Played Man with No Name in Various Decades?

James Cagney

as 1930s in What Actors Could've Played Man with No Name in Various Decades?

Gary Cooper

as 1920s in What Actors Could've Played Man with No Name in Various Decades?

Diablo Cody

as Writer in Betty Grable: America's Sweetheart

Martin Scorsese

as Director in Betty Grable: America's Sweetheart

Bryan Cranston

as Darryl F. Zanuck in Betty Grable: America's Sweetheart

Tom Hanks

as John Grable in Betty Grable: America's Sweetheart

Annette Bening

as Lillian Grable in Betty Grable: America's Sweetheart

Diego Luna

as Cesar Romero in Betty Grable: America's Sweetheart

Emma Stone

as Beverly Stovenour in Betty Grable: America's Sweetheart

Chris Evans

as Harry James in Betty Grable: America's Sweetheart

Margot Robbie

as Elizabeth Grable in Betty Grable: America's Sweetheart

Aaron Sorkin

as Writer in Judy Tyler: A Star's Journey

Martin Scorsese

as Director in Judy Tyler: A Star's Journey

Bradley Cooper

as Rollo Thorpe in Judy Tyler: A Star's Journey

Hugh Jackman

as Edward Sullivan in Judy Tyler: A Star's Journey

Austin Butler

as Elvis Presley in Judy Tyler: A Star's Journey

Tom Hanks

as Robert Schmidt in Judy Tyler: A Star's Journey

Timothée Chalamet

as Earl Gregory Nisonger Jr. in Judy Tyler: A Star's Journey