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Pop sensations Alvin, Simon and Theodore end up in the care of Dave Seville's twenty-something nephew Toby (Levi). The boys must put aside music superstardom to return to school, and are tasked with saving the school's music program by winning the $25,000 prize in a battle of the bands. But the Chipmunks unexpectedly meet their match in three singing chipmunks known as The Chipettes -– Brittany, Eleanor and Jeanette.

The Chipmunks act began with recordings first brought to life in Bagdasarian's 1950s novelty recordings under the name David Seville and the Chipmunks. For stage purposes, such as during an appearance on The Ed Sullivan Show, Bagdasarian lip-synched the words of "David Seville" in front of a small puppet theater, with puppets of the three Chipmunks also lip-synching. The puppets looked similar to the Chipmunk illustrations on the covers of some of the group's 45 RPM records. The characters were an unprecedented success, and the singing Chipmunks and their manager were given life in several animated cartoon shows, using redrawn, anthropomorphic chipmunks, and eventually motion pictures.

The voices of the group were all performed by Bagdasarian, who sped up the playback to create higher pitched voices. This oft-used process was also not entirely new to Bagdasarian, who had also used it for two previous novelty song projects, including "The Witch Doctor," but it was so unusual and well executed it earned the trio two Grammy Awards for engineering. Although the characters were fictional, they did release a long line of actual albums and singles, with "The Chipmunk Song" becoming a number-one hit single in the United States.