One Crazy Summer (1986)

Tagline: "They're out of school, out on Nantucket, and out of their minds. With this crowd, anything can happen!"
Cusack plays: 'Hoops' McCann - who leaves behind Generic, New York to spend the summer on Nantucket and work on his entry for a scholarship to Design School.

From the same director as Better off Dead - 'Savage' Steve Holland and containing some similar quirks, such as animations and bizarro moments. Lets just say I'm not in any kind of rush to watch this again. Ever. I'm not big on 'wacky' comedies. This film sees the first time JC appears with fairly frequent co-star Jeremy Piven, and Demi Moore sings. Not too much else of note I'm afraid. Lots of crazy plans ensue to beat the bad guys and save Demi's dead grandads house from developers.

The trailer might actually be funnier than the film:

Stand by Me (1986)

Tagline: For some, it's the last real taste of innocence, and the first real taste of life. But for everyone, it's the time that memories are made of.
Cusack plays: Denny Lachance, deceased older brother of central character Gordy.

This is Cusack's second film for director Rob Reiner (after The Sure Thing), although he appears in only a couple of flashback scenes as the dead big brother who Gordy feels he will never live up to, and was kinder to him than his parents. The film is a 80's classic with brilliant central peformances from the four young actors in the central roles. Its always sad to watch the River Pheoenix scenes, such a talent. Four kids (with baggage eg a crazy father, fatness, from a family of criminals) travel to find the dead body of a local boy in the woods. They contend with their issues and nasty bully Keifer Sutherland along the way.