It's hard to imagine—especially after two consecutive summers headlining the biggest film in the world—that until his first turn as Tony Stark, Robert Downey Jr.'s biggest hit was Rodney Dangerfield's Back to School, the story of a party-hardy old man who goes to college to help his idiot son fit in. Though this 1986 film hasn't aged particularly well (really, has anything starring Dangerfield, Caddyshack included?), there are some capsule moments that make the late-summer mainstay a classic, among them cameos by Kurt Vonnegut and Oingo Boingo. And, of course, there's Downey, honing his trademark smugness decades before he rose to leading-man status and earned the respect that had often eluded him…but, for some reason, clung to Dangerfield despite his claims to the contrary.

  • Showing at: Laurelhurst.
  • Best paired with: Coalition Simple ISA.
  • Also showing: Grease (Academy), The Way, Way Back (Hollywood).