Lots of guys used to dream about having a date with Marilyn Monroe, but three friends who are about to graduate from high school to go their separate ways try to make that fantasy a reality in this comedy, set in 1962. Roy (Jason Priestley), Ned (Gabriel Olds), and Scott (Jerry O'Connell) have been buddies since the age of six, when they were entered together in a Howdy Doody look-alike contest. With only a few weeks to go before they graduate from high school, Roy has impulsively joined the Army to get away from his abusive father, while Ned has discovered he's going to be a father, and Scott is still plagued by his pesky virginity. Wanting to enjoy their last few weeks of freedom, Roy "borrows" a wad of cash and a blue Galaxie 500 convertible from his former employers, repo men Arturo and Antonio Gallo (Kurt Fuller and Stephen Tobolowsky), and persuades his friends to join him as he heads to Hollywood. Roy wants to meet the woman of his dreams, Marilyn Monroe, whom he's learned is working on a new picture, Something's Got to Give. With the help of Roy's Uncle Harry (Joe Pantoliano), they locate Monroe's home and camp out at her gate, hoping to get a glimpse of the glamourous goddess. However, Roy breaks out a reefer to smoke while they attempt to stay up all night (tactical error number one: marijuana does not make you more alert!), and when she slips out without their noticing, the three end up on a mad chase to find Marilyn before she gets away. Meanwhile, the Gallo Brothers have noticed their car is gone, and they are determined to get it back, without much concern for the health or safety of the thief. Calendar Girl was Jason Priestley's first vehicle following his success on the television series Beverly Hills 90210.