- Jason Robards played the role of Hickey in multiple stage productions and the 1960 TV adaptation.
- Tom Pedi played the role of Rocky the bartender in the original 1947 stage production, the 1960 TV adaptation and the 1973 film adaptation.
- Sorrell Booke played the role of Hugo Kalmar in both the 1960 TV adaptation and the 1973 film adaptation.
- Robert Redford played the role of Don Parritt in the 1960 TV adaptation.
- James Earl Jones played the role of Hickey in the 1973 stage production.
- Jeff Bridges played the role of Don Parritt in the 1973 film adaptation and Lee Marvin played Hickey.
- Denzel Washington played the role of Hickey in the 2018 stage production.
- Austin Butler played the role of Don Parritt in the 2018 stage production.
- Kevin Spacey played the role of Hickey in the 1999 Broadway and London Old Vic Productions.
- Nathan Lane played the role of Hickey and Brian Dennehy played Larry Slade in the 2012 Goodman Theater production, which was revived in 2015 at BAM.
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