The tree that the chipmunks Alvin and the Chipmunks live in is cut down and driven to Los Angeles. After JETT Records purchases it as a Christmas tree, the Chipmunks meet the struggling songwriter and composer, Ross Bagdasarian, Sr., who has had his latest song rejected by the company's chief executive, Ian Hawke, his former college roommate and best friend, who claims that there is "no sense in writing songs that no one is ever going to sing." Dave also once had a relationship with his next door neighbor, Claire Wilson.