One Crazy Summer (1986) – Nostalgia Central

Hoops McCann (John Cusack) and his pal George Calamari (Joel Murray, Bill’s younger brother) graduate from Generic High School.

Hoops is from a basketball family but lacks interest and talent and wants to be an artist. His audition for the Rhode Island School of Design is to write and illustrate a love story. But he’s never been in love, so a love story is a tough challenge.

George persuades Hoops to spend the summer on Nantucket Island, where that situation is sure to be remedied.

Along the way, they rescue hippie singer Cassandra Eldridge (Demi Moore) from a herd of bikers.

She is headed to Nantucket to save her late grandparents’ house – but the back mortgage is $3,000, and she has just a week to scratch up the money.

If she loses the house, her grandparents’ elderly friends will be tossed out, and it will be razed by rampaging, venal, heartless developer Aguilla Beckersted (Mark Metcalf) to be part of square miles of crowded, tacky condos.

But Aguilla’s wheelchair-bound father (William Hickey) has said he will disinherit his son and grandson if the two do not win the annual regatta.

Meanwhile, George’s unkempt, spacey chronic loser cousin Ty (Jeremy Piven) has spent the entire summer by the phone and radio, sacrificing everything so he can be the 50th caller to a radio jingle contest and win $1 million.

Rounding out the cast are Bobcat Goldthwait and Tom Villard, as the bizarre Stork twins, a pair of unmatched tweedle-dees with manic overtones; Curtis Armstrong as timid seashell collector Ack Ack, son of red-blooded Marine General Raymond (Joe Flaherty), and Kristen Goelz as George’s bespectacled kid sister, Squid.

The Stork twins, George, Hoops and Ack Ack renovate a rotted boat and enter the regatta in an attempt to help Cassandra save her grandfather’s house.

With quilted, patchwork sails flying, a stolen Ferrari motor under their stern, and a dog as their masthead, the boys blast by the Beckersted clan and take the checkered flag.

There are a lot of gaps in the story, and some of the sight gags aren’t all that funny, but all this is a semi-sweet little film that is a whole lot less painful than most 1980s summer movie fare.

Hoops McCann
John Cusack
Cassandra Eldridge
Demi Moore
Mrs McCann
Linda Warren
George Calamari
Joel Murray
Egg Stork
Bobcat Goldthwait
Squid Calamari
Kristen Goelz
Clay Stork
Tom Villard
Ack Ack Raymond
Curtis Armstrong
Andrea
Jennifer Yahoodik
Brunhelda
Rachel C. Telegen
Stain
John Matuszak
Teddy Beckersted
Matt Mulhern
Aguilla Beckersted
Mark Metcalf
Old Man Beckersted
William Hickey
Cookie Cambell
Kimberly Foster
Ty
Jeremy Piven
Ty’s Girlfriend
Lisa Melilli
Grandma
Billie Bird
Uncle Frank
Bruce Wagner
General Raymond
Joe Flaherty
Yuppie Preacher
Al Mohrmann
Taylor
Taylor Negron
Wilbur
Rich Hall
Chrong Freen
Donald Li
Graduation Orator
Grenville Cuyler
Crossing Guard
Laura Waterbury
Giant
Barry Doe
Disc Jockey
Rich Little
Boscoe
Sky

Director
Savage Steve Holland

Video