All freshman year Jack Donnigan wanted to ditch the nerds and become cool. When Jack-a protected 16-year-old sophomore at St. Andy's Prep in Southern California in 2000-gets accepted into The Crew, a renegade punk clique on campus led by the nefarious and intelligent Cannonball ("Cannon"), he is thrilled. But he soon challenges Cannon's leadership by starting a secret relationship with Sarah-a punk-feminist who Cannonball mysteriously says is off-limits-trying hard drugs, and jumping on stage at punk shows.
Jack's relationship with Mom becomes strained. He stays out late and rebels for the first time. The faculty at St. Andy's-wanting to dismantle the cult hero status of The Crew-organize a coup. They plan to nail the perceived leader: Jack Donnigan, who's been conned by Cannonball. Jack's mentor is his unconventional English teacher, Mr. Bryce, who teaches Jack a more nuanced world view.
When the faculty nail Jack, Mr. Bryce does his best to save the floundering student. But when Jack is kicked out of his folks' home, expelled from school, and Cannonball steals Sarah by spreading a web of lies: Who will save Jack from himself?