Aspiring cartoonist Hoops McCann (John Cusack) really wants to write and illustrate a cute love story but can't seem to get his life together. Seeking inspiration he sets off to spend the summer on Nantucket with his friend George Calamari (Joel Murray) and the latter's near-mute kid sister Squid (Kristen Goelz) who brings along her crippled dog, Boscoe. Along the way Hoops saves the lovely Cassandra Eldridge (Demi Moore) from a dangerous motorcycle gang. Cassandra wants to be a singer but right now she's battling to save her late grandfather's house from the greedy Beckersted family. Hoops enlists an assortment of wacky friends to help Cassandra out and eventually what he has been searching for.
One Crazy Summer was the second film John Cusack made with quirky writer-director, producer and animator Savage Steve Holland. Which must have made for an awkward situation. Midway through filming Cusack reacted badly to a test screening of their first movie Better Off Dead (1985) which he not only described as the worst movie he had ever seen but told Holland he would never again trust him as a director. In recent years Cusack has admitted he overreacted and felt that way about all his movies. Still one cannot help but question his taste given both films remain seminal Eighties teen comedies and arguably exerted no small influence upon Cusack's similarly off-kilter, self-scripted cult comedy Grosse Point Blank (1997).
Sadly the (in retrospect, surprising) box office failure of One Crazy Summer followed by that of the later How I Got Into College (1989) soured Steve Holland on big screen filmmaking for the next twenty years or so. Cinema's loss proved children's television's gain as Holland went on to create and direct numerous animation series, sitcoms and TV movies for both the Disney Channel and Nickelodeon network right up to his recent good-natured boy band parody Big Time Rush. There is a surreal flavour to the cartoonish parallel worlds Holland creates onscreen that means his work has dated a lot better than some films by his overpraised contemporary John Hughes. Zany yet oddly heartfelt, One Crazy Summer crams in as many fast-paced gags, both visual and verbal, as the frame will allow much like the copy of Mad magazine two characters are glimpsed yokking over in one scene.
Yet amidst an abundance of winningly silly humour (e.g. Bobcat Goldthwait in a Godzilla costume stomping a model city; the uncle glued to the radio in the hope of winning a contest; the two little girls whose funny faces stay that way just as the grownups warned them) a genuine theme emerges depicting a world that seems overwhelming, strange and often ridiculous to the young heroes grappling with what to do with their lives post-high school. Several sub-plots concern father issues with both town bully boy Teddy Beckersted (Matt Mulhern) and comic side character Ack Ack Raymond (Curtis Armstrong) – Holland has a penchant for wacky character names - frustrated in trying to prove themselves to their overbearing dads. Given Holland was once an aspiring animator and includes a character inspired by his real-life sister (who cameos here) there is likely a semi-autobiographical element. Additionally the film depicts the central love story with a disarming degree of tenderness underlined by some eye-catching and inventive animated sequences that offer a window into Hoops' ongoing anxieties. How many other quirky comedies are as earnest in their belief in the importance of true love? Nevertheless, One Crazy Summer is a less nuanced comedy than Better Off Dead, focused primarily on pitching an endless assault of gags. On that count it undeniably delivers with the entire cast including Cusack and Demi Moore (proving she can do comedy) more than up to the task of keeping the laugh rate consistently high.