Tom Cruise wears a Rolex Air-King

Brian Flanagan wants to get rich and has no real plan for how. Roger Donaldson directed Cocktail (1988) as a star vehicle for Tom Cruise fresh off Top Gun: a young Army veteran tends bar in Manhattan, decamps to Jamaica, falls in love, and eventually opens his own place. Critics savaged it; audiences made it one of the year's biggest hits.

On Flanagan's wrist is a Rolex Air-King, the entry point to the Oyster Perpetual line, with a clean silver dial and a 34mm steel case. It sits below the Datejust and well below the Submariner in both price and prestige, the most modest Rolex a man can wear and still be wearing a Rolex.