Taking a look at the cast, one would think this should be an easy win, but somehow it manages to take a simple story and makes it impossible to care about what happens.
The real problem here is the movie is weighed down by too much and it never gets to build up any speed, it just unfolds and unfolds, yet doesn't get anywhere.
So, let's take a look at what I'm talking about: There are too many characters within, and as a result the plot is muddy. Whose story is this? Is this about Hoops, and what he wants to do with his life? Is it about Cassandra's house? Is it about Hoops, and Cassandra's nascent romance? Is it about Hoops and his oddball friends? Is it about any one of these people, and their battle with a family of rich narcissists? If you consider that it's trying to be all of the above, you can understand why it's so clunky.
If this wasn't bad enough, there are several running jokes throughout. Would it have merely been one, and had it been fleshed out properly, it could have worked, but that's not what happened. Just to name two: the little girl's dog, and the Beckersted lobster fascination. How high was the writer/director?
Too much going on. No through line. Jokes that crash and burn before they even get off the ground.
Now, there was one funny part, and that's when Bobcat Goldthwait gets stuck inside a Godzilla costume and crashes a party.
I can see that _One Crazy Summer_ was trying to make a zany comedy like _Caddyshack_ (1980) or _Revenge of the Nerds_ (1984), but lacked the direction and cohesion to make it work.
I can't recommend this. Too many great '80s comedies out there to waste your time watching this.

Post script: Since I already mentioned Aguilla Beckersted's obsession with lobsters, I'll reiterate that the joke doesn't work. However, what it does manage is to convey that the man is a psychopath who derives pleasure from torturing lobsters. The problem here is in three scenes, live lobsters are used. I'm giving the movie the benefit of the doubt here that they didn't actually boil one alive for this shitty movie. In another scene, we see Aquilla kick a dog - again, to convey that the man has zero empathy. Now, the scene is shot so you don't actually see him kick the dog, because if the actor actually did that, people would lose their minds. I want you to think about that: kicking a dog is wrong, yet boiling a lobster to death is fine. This is the very definition of speciesism.
Animals are here with us, not for us.

Liked this quite a bit. The humor is right up my alley with the absurd mixed with the traditional (kind of reminds me of Caddyshack in a way). John Cusack's style was great and although admittedly didn't have great chemistry with Demi Moore, I did laugh enough that I had a good time. Just an easy-going film and a perfect watch to end the summer. **3.75/5**