One Crazy Summer

A 1986 Screwball Comedy starring John Cusack and Demi Moore. The plot focuses on the antics of "Hoops" McCann (Cusack) and his friends as they spend a summer cavorting around the island of Nantucket, Massachusetts. Sometime along the way Hoops and his friends run across a young rock singer named Cassandra Eldridge (Moore) whom they must help to save her grandmother's house from the clutches of Aquilla Beckersted and his son Teddy.

Tropes used in One Crazy Summer include:

Animated Credits Opening: Both the opening and closing of this film are animated. The director, Savage Steve Holland, is also an animator.
Chekhov's Gun: Hoops' fear of boats is mentioned at the beginning, naturally the climax revolves around boats.
Chekhov's Skill: Inverted in that Hoops is established to have absolutely no basket-making (as in basketball) ability, but is called upon to sink a ridiculously difficult shot at the climax.
Cone of Shame: Worn by Squid's dog Bosco, and also by Bosco's pups in the final moments of the film.
Cute Is Evil: The "Cute and fuzzy bunnies" from Hoops' animated story.
Idle Rich: Teddy.
Ironic Nickname: Despite his name, Hoops is terrible at basketball.
Jerk Jock: Teddy.
Kaiju: See "Shout Out" on the Trivia page.
Kick the Dog: The villain literally kicks a dog as part of his over-the-top characterization. He also likes to listen to lobsters scream as he boils them.
Nautical Knockout
Never Say That Again: The very mention of the word "work" is enough to make idle rich snob Teddy clutch his ears in terror.
Non Sequitur Scene: Used in-universe when, during a Rousing Speech, Hoops rails against the "Cute and fuzzy bunnies," eliciting looks of confusion from his friends.
Overlord, Jr.: Teddy to Aquilla.
Scale-Model Destruction: See Shout-Out on the Trivia page.
Searching the Stalls: The leader of a biker gang opens each stall and finds the person he was looking for in the last one.
Take That: Siskel and Ebert gave Savage Steve Holland's previous film Better Off Dead a negative review, so at the end of the movie a pair of "Cute and fuzzy bunnies" who resemble them get blown up.
The Precious, Precious Car: Teddy's red Ferrari, complete with Vanity License Plate.
Vanity License Plate: On Teddy's car, "CUL8R"
Wastebasket Ball: Hoops plays a game of this just after producing another failed cartoon. The wastebasket, which is surrounded by a couple dozen crumpled-up papers, is completely empty.
Why Did It Have to Be Snakes?: Hoops is terrified of water and of traveling by boat; seeing as the movie takes place in Nantucket (a city that is on an island) and culminates in a boat race, this is a fear he has to overcome.