Comedy
United States of America
The successful author in question is Henry McCarthy, played by Mark Polish. He's written a best-selling novel that's become a pop culture phenomenon, but he's struggling with writer's block as he tries to follow it up. While he's back in his hometown for the commencement address, he has to contend with a number of people from his past—including the aforementioned Shasta O'Neil, played by Winona Ryder. Shasta is still beautiful and flirtatious, but unwisely involves Henry in her ongoing marital drama with her high school sweetheart, played by Josh Holloway.
Meanwhile, Henry's former English teacher, played by Chevy Chase, encourages him to reconnect with his past in the hopes of finding fresh inspiration. Henry reconnects with his old high school friends, played by Sean Astin and Hilary Duff, and they help him remember what it was like to be carefree and creative in his youth. However, the author also has to deal with the fact that his high school crush, Scarlet Smith, played by Famke Janssen, is now married and has a child.
Throughout the film, Henry struggles to balance all of his conflicting feelings and responsibilities, including his obligations as a successful author and his personal desires and insecurities. Stay Cool is a bittersweet comedy that examines themes of nostalgia, regret, and the difficulty of growing up.
