Sean Penn wears a Rolex Day-Date

Sean Penn disappears into David Kleinfeld so completely that you almost forget he is the same actor. Brian De Palma's Carlito's Way (1993) follows Al Pacino's Carlito Brigante, a drug dealer trying to go straight in late-1970s New York, but the film's most volatile presence is Penn's Kleinfeld, Carlito's cocaine-addled lawyer, whose schemes keep pulling his client back into the world he is trying to leave. Penn plays him with a receding hairline, tinted glasses, and the jittery energy of a man running on chemicals and fear.

On Kleinfeld's wrist is a gold Rolex Day-Date, the right watch for a lawyer living beyond his means. Rolex has made the Day-Date only in gold or platinum since 1956, and its association with mid-century presidents earned it the informal name "President." By the late 1970s it was a default status watch, success made visible from across a room. The gold case is clear on screen, though the cuff hides the dial, and the Day-Date identification comes from watch-spotting write-ups rather than a documented production source.