William is a brilliant 15 year old music critic who gets hired by "Rolling Stone" magazine to write an article about Stillwater, an up and coming rock band on a tour across the US. William joins them on the tour becoming friends with the band and their groupies, particularly with Russel Hammond (Billy Crudup), the charismatic and enigmatic lead guitarist of the band, and Penny Lane (Kate Hudson), one of the groupies and Russel's lover. Russel, however, already a girlfriend who will join the band in New York and Penny Lane knows that she will have to leave.

In the previous scene the members of the band play a game of poker with the band Humble Pie, putting up their groupies as a stake and losing them for 50 dollars and a case of beer.

When Penny Lane tells William (who is in love with her) that she is thinking to go to New York with the band, William flips out and tells her to wake up about her relationship with Russel, who sold her for "50 bucks and a case of beer"...