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Side-by-Side Photos of Actors Portraying Iconic Old Hollywood Stars

Esquire Logo By Janaya Wecker of Esquire | Slide 3 of 41: Don Cheadle stunned audiences as Sammy Davis Jr. But it wasn't easy preparing to step into the singer's legendary shoes—in the weeks leading up to filming, Cheadle learned to sing, tap dance, play drums, play trumpet, and twirl six-shooter pistols. Shop Now

Don Cheadle as Sammy Davis Jr.

Don Cheadle stunned audiences as Sammy Davis Jr. But it wasn't easy preparing to step into the singer's legendary shoes—in the weeks leading up to filming, Cheadle learned to sing, tap dance, play drums, play trumpet, and twirl six-shooter pistols.

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