Tom Cruise wears a Rolex Day-Date

Charlie Babbitt sells exotic cars to people who can't afford them and talks his way through every situation he encounters. Tom Cruise plays the Los Angeles hustler in Barry Levinson's 1988 drama, a man who discovers at his estranged father's funeral that he has an older brother, Raymond (Dustin Hoffman), an autistic savant living in an institution. When Charlie learns that Raymond is the sole heir to their father's three-million-dollar estate, he takes his brother on a cross-country road trip that begins as a kidnapping and turns into something else.

The Rolex Day-Date on Cruise's wrist is the watch you buy when you want everyone to know you have made it: solid yellow gold, President bracelet, the day of the week spelled out at twelve. It fits a man who leases Lamborghinis he can't pay for and promises delivery dates he can't meet, projecting success to keep the hustle alive. Halfway through the film Charlie pawns it in Las Vegas to bankroll the card-counting spree with Raymond, then buys it back for $3,500 out of their $86,000 in winnings.