Making the Grade (1984)

Lazy preppie Palmer Woodrow hires street-smart Eddie Keaton to go to school for him while he lives it up in Europe. Eddie falls in love with preppie gal Tracey, upsetting Biff, the Hoover Academy bully. When his bookie from the old neighborhood, Dice, comes to collect on Eddie's gambling debts and Palmer returns early from Europe, the the scheme slowly starts to unravel. Soon, Eddie can't even tell whose side he's really on.