Carlito's Way chronicles the life of a Puerto Rican gangster who pledges to turn his life around and retire in paradise, but finds that life rarely goes according to plan. Who portrays Carlito's lawyer and best friend David?

Answer Sean Penn

Sean Penn portrays David Kleinfeld, Carlito's unscrupulous lawyer, and closest buddy. Sean Penn and Palma got together and analyzed the appearance of the 1970s mafia attorneys. They discovered that those lawyers were stranger than the drug lords they were representing. That's why Penn cut his frontal hairline - to appear weirder.

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