Thirteen years after getting out of school where his P.E. teacher, Jasper Woodcock (BILLY BOB THORNTON), constantly belittled him and the other boys, John Farley (SEANN WILLIAM SCOTT) is a successful author whose self-help book, "Letting Go: How to Get Past Your Past" is based on finally getting over the trauma Woodcock created for him.
Now traveling about the country with his manager/publicist, Maggie (AMY POEHLER), John decides to take a break and visit his long-widowed mother, Beverly (SUSAN SARANDON), in his hometown of Forest Meadow, Nebraska. There, he's surprised to hear that she's been dating a guy for five months, but is then horrified when he learns that it's Mr. Woodcock.
The coach doesn't remember John, but misses nary a beat in returning to form by picking up where he left off in belittling him. Thus, and despite former classmate turned teacher Tracy (MELISSA SAGEMILLER) showing some interest in him, John focuses on getting even with his former coach. With the help of fellow former student and Woodcock sufferer, Needleman (ETHAN SUPLEE), John sets out to derail his mom's relationship with his childhood tormentor.