Almost Famous (2000)
Synopsis: "In this enchanting coming-of-age story based on director Cameron Crowe's own experiences, teenage writer William Miller (Patrick Fugit) cajoles a Rolling Stone editor into handing him a plum assignment to cover the band Stillwater on a cross-country tour. Kate Hudson earned an Academy Award nomination for her portrayal of band groupie Penny Lane, while Crowe won the Oscar for his original script. Jason Lee and Billy Crudup co-star."
Synopsis compliments of Netflix