Calendar Girl is a 1993 American comedy film directed by John Whitesell and starring Jason Priestley, Gabriel Olds, and Jerry O'Connell. The film, set in the 1950s, revolves around three teenage boys who embark on a road trip from their hometown of Boise, Idaho to Hollywood, California with the intention of meeting Marilyn Monroe.
Roy Darpinian is a sixteen-year-old boy who has an intense infatuation with Marilyn Monroe. He convinces his two best friends, Scott Foreman and Ned Bleuer, to join him on a summer road trip to Hollywood, where he hopes to meet Marilyn and become her friend. The boys set out in Roy's father's Cadillac, with nothing but a vague plan and a lot of determination.
Along the way, they encounter a series of mishaps and adventures. They are chased by the police, rescue an elderly woman from a burning building, and meet a group of young women who join them on their journey. Despite these distractions, Roy remains focused on his goal, even going so far as to break into Marilyn's house in the middle of the night.
Eventually, the boys manage to meet Marilyn at a Hollywood party. Roy impresses her by rescuing her from a pushy suitor, and she invites him to be her escort to a movie premiere. Although their time together is brief, Roy feels that he has achieved his dream of meeting Marilyn and has gained a more realistic perspective on life.
The film concludes with the boys returning home from their adventure, changed by their experiences and ready to face the challenges of adulthood.