18. 'Big Shot' (Dir. Kevin Connolly)
The title character in Big Shot is one of 30 For 30's unlikeliest subjects: John Spano, a wheeler-dealer who promised to be the savior of a moribund New York Islanders franchise, only to be exposed as a fraud after he'd "bought" the team. Professional sports ownership is an exclusive club, one which Spano desperately wanted to join, even if it meant hatching an ill-conceived plan that would've seen him use revenue from the Islanders to pay what he owed. The whole scheme speaks to the power of the luxury box, and the desire of some people to buy their way into a world they're otherwise not gifted enough to join.