Max Fisher, a talented and aspiring teenager (Jason Schwarzman Jason Schwartzman), attends an aristocratic preparatory school in Houston. Max, who just entered a prestigious school, devoted all his mind to the club. With his extraordinary intelligence, he soon became adept at various societies. However, overly neglecting his homework, he soon faced the threat of being expelled from school. As a result of fate, he and the successful business tycoon Herman Bloom (Bill Murray Bill Murray) became lost friends and learned a lot of life truths. However, it all ends up in the hands of talented and good-looking female teacher Ruth Mary Kross (Olivia Williams Olivia Williams). Max is so caught up in the world of love that he can't extricate himself. With its tit-for-tat witty dialogue and sense of humor, as well as the successful shaping and interpretation of roles by new and old actors, the film won many awards such as Best supporting Actor in the 56th Golden Globe Awards in 1999 and Best Director and Best supporting Actor in the Independent Spirit Award in 1999.