In 1973, William Miller (Patrick Fugit), is a 15-year-old boy aspiring to be a rock journalist. Unfortunately for William, his mother, Elaine (Frances McDormand), is determined that William will be the country's youngest lawyer, and has skipped the 'predominantly advanced' boy a couple of grades in school and while at home, she thinks, she provides him the tools he needs to be a success. These 'tools' are of more value to him, she believes, than merely fitting in with a crowd. William rises up to the responsibility of using his intelligence, though not as his mother hopes. Shunned by his classmates (most of whom are two or three years older than he is), he writes for underground papers in his hometown of San Diego, sharing the love of rock and roll instilled in him through a farewell gift of music from his sister, Anita (Zooey Deschanel): albums left behind on the day that she escapes the home life which William must still endure.

He goes one morning to watch as a local radio station interviews pioneering rock journalist Lester Bangs (Philip Seymour Hoffman). William has been sending Bangs copies of his work, and Bangs recognizes the talent of the boy. The two hit it off, and Bangs gives William a $35 assignment to write up a Black Sabbath concert. Lester advises William to be honest and unmerciful, but fails to mention how to get into the show or to meet the band. William, without credentials or a ticket, cannot get into the arena. He meets up with some semi-groupies who call themselves "Band-Aides": Estrella Starr (Bijou Phillips), Polexia Aphrodisia (Anna Paquin), Sapphire (Fairuza Balk), and their leader, Penny Lane (Kate Hudson). The Band-Aides gain entrance to the show, but William is still barred from entry as the opening band, Stillwater, arrives, running late. At first they dismiss him as a journalist, "the enemy", but when he calls them by their names and praises their most recent work in detail, they realize that he is a genuine fan and maneuver him backstage. There, in spite of his instincts, the band's "guitarist with mystique", Russell Hammond (Billy Crudup) takes a liking to William, no doubt in part because of William's apparent friendship with Penny, and invites William to meet up with him and the band again.
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