One Crazy Summer (1986)

Holland’s second feature after Better Off Dead, and the second half of the unofficial Cusack-Holland comedy diptych. Same screwball DNA, different setting, a Nantucket summer full of cartoon gags, sailing races, and a romance that exists mostly so the cartoon gags have an excuse to escalate.

Why it’s in the canon

80s comedy comfort film, Holland’s screwball Nantucket energy. The criteria blend is 1+3, I loved it, and I want to remember it. This is not great cinema, and it isn’t trying to be. It’s a fun comedy from the 80s that I really enjoyed, and re-watching it puts me back in that register, easy, smiling, in on the joke.

What the film does

A cartoonist (Cusack) follows a woman to Nantucket and gets tangled up with a corrupt real-estate developer and the town’s annual sailing regatta. Holland, an animator by training, keeps dropping hand-drawn asides and visual non-sequiturs into the live action. The plot is a delivery vehicle for gags, and the film knows it.

What stays with me

The tone. Holland’s comedies don’t sweat whether you take them seriously. They earn affection by being exactly what they are, no apology, no winking. The 80s is full of comedies that tried to be Caddyshack and landed somewhere brittle; this one lands somewhere warm.

On hand

Yes, physical DVD + digital.