Movie Review: One Crazy Summer (1986)

★★★★★

One Crazy Summer is just that crazy, weird, and totally fun. It’s like a cartoon come to life with 80s vibes all over.

Sam R.

South Carolina

If you’ve never seen One Crazy Summer, the title tells you most of what you need to know, but not in the way you think. Sure, it’s set in the summer, and yes, things get crazy, but it’s not just your average “beach party” movie.

Rewatching it for BoxReview.com, I was reminded that this is one of those mid-’80s comedies that doesn’t mind being completely silly one moment, genuinely sweet the next, and then totally surreal right after that. And it works because it’s having fun with itself the whole time.

The Premise: Summer Plans Go Sideways

The story follows Hoops McCann (John Cusack), a recent high school grad who’s reluctantly heading to Nantucket with his buddy George (Joel Murray). Hoops has big dreams of becoming a cartoonist, but he’s suffering from a serious case of self-doubt.

Once on the island, they run into Cassandra (Demi Moore), a singer trying to save her grandfather’s home from being bought out by the wealthy Beckersted family. Naturally, there’s a regatta involved (because in ’80s comedies, there’s always a regatta), and Hoops ends up helping Cassandra in her fight.

That’s the basic framework, but honestly, the joy of One Crazy Summer is in everything that happens between those plot points.

John Cusack: The Reluctant Hero

Coming off Better Off Dead, Cusack once again plays the awkward, good-hearted lead who gets pulled into a bizarre situation. What’s interesting here is that Hoops isn’t a “man of action,” he’s more of a “man of reluctant reaction.” He doesn’t charge into situations; he gets swept into them.

That slightly passive energy makes his eventual stand in the regatta finale feel earned. And Cusack’s natural charm keeps you rooting for him, even when he’s clearly in over his head.

Demi Moore Before the Big Break

Before Ghost and A Few Good Men, Demi Moore was showing early star power in roles like Cassandra. She plays it straight here, which is smart because she’s the grounding force amid the cartoonish chaos swirling around her.

It’s worth noting that her music subplot isn’t just window dressing. Cassandra’s performances and fight to save her home give the movie a little emotional weight that keeps it from floating away in silliness.

The Comedy: Savage Steve Holland’s Signature Weirdness

Director Savage Steve Holland has a very specific comedic style, part slapstick, part surrealism, part “did that just happen?” One Crazy Summer has:

• Running gags — like the Stork twins, who seem to live in their own bizarre cartoon reality.

• Over-the-top villains — Mark Metcalf (yes, Niedermeyer from Animal House) as Beckersted Jr. is just the right kind of smarmy.

• Physical comedy — exploding lobsters, wild chase scenes, and elaborate sight gags.

• Cartoon cutaways — literally, as Hoops’ drawings come to life on screen, giving us peeks into his creative mind.

That last part is important. The animation sequences aren’t just a gimmick; they underline the fact that Hoops sees life like a cartoon, even if he doesn’t always act like the hero in one.

Joel Murray and the Supporting Cast

Joel Murray’s George is one of the film’s underrated gems, a nervous, lovable sidekick who always seems one step away from total panic. Add in Bobcat Goldthwait in full ‘80s Bobcat mode (including one scene where he’s trapped inside a Godzilla costume), and you’ve got a supporting cast that can carry entire scenes without Cusack or Moore even present.

The Villains: Cartoonish but Effective

The Beckersteds are exactly what you want in a summer comedy villain family: wealthy, snobbish, and dripping with overconfidence. They’re not meant to be realistic threats; they’re there to be booed, hissed, and (eventually) laughed at when they get their comeuppance.

Under-Discussed Element: The Heart Beneath the Absurdity

It’s easy to get distracted by the slapstick and animated bits, but at its core, One Crazy Summer is about self-confidence and the idea that you don’t have to be a traditional “hero” to do something heroic.

Hoops’ journey is less about winning the regatta or getting the girl, and more about realizing he can step up when it matters, even if it’s in a goofy, unpolished way.

The Regatta Finale: Peak ’80s Comedy Climax

The final boat race is pure Savage Steve Holland part sports underdog story, part total chaos. It’s absurd, overblown, and exactly the right payoff for the Beckersteds’ smugness.

Even though you can guess how it’ll end, the fun is in how it gets there. It’s like a live-action cartoon where every gag you can imagine gets thrown into the mix.

Themes That Still Resonate

• Being okay with your own weirdness — Hoops doesn’t “become cool” by the end; he just owns who he is.

• Friendship as the real prize — the ragtag group that bands together feels like the real win.

• Poking fun at the rich — some targets never go out of style,

Why One Crazy Summer Still Works

It’s not trying to be a big statement about youth or romance. It’s not aiming for realism. It’s aiming to make you smile for 90 minutes, and it does that by throwing every kind of joke at you, visual gags, running jokes, and absurd situations until something lands.

Like its predecessor, Better Off Dead, it’s the kind of movie that grows on you. You might watch it once for the laughs, but it’s the weird little details you’ll remember years later.

Final Thoughts

One Crazy Summer is like a snow cone on a hot day, colorful, a little messy, and exactly the kind of treat you don’t have to overthink to enjoy.

If you’re in the mood for an ’80s summer comedy that doesn’t take itself seriously for even a second, it’s worth tracking down. Just be ready for Godzilla suits, cartoon lobsters, and one of the most delightfully odd regatta races ever filmed.