A struggling songwriter named Dave Seville finds success when he comes across a trio of singing chipmunks: mischievous leader Alvin, brainy Simon, and chubby, impressionable Theodore.
Pop sensations Alvin, Simon and Theodore end up in the care of Dave Seville's twenty-something nephew Toby. The boys must put aside music super stardom 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. Romantic and musical sparks are ignited when the Chipmunks and Chipettes square off.
Through a series of misunderstandings, Alvin, Simon and Theodore come to believe that Dave is going to propose to his new girlfriend in New York City - and dump them. They have three days to get to him and stop the proposal.
Playing around while aboard a cruise ship, the Chipmunks and Chipettes accidentally go overboard and end up marooned in a tropical paradise. They discover their new turf is not as deserted as it seems.
While the Chipmunks are working at the amusement park, Majestic Movie Studios, in a singing attraction. Little do they know that the real Dr. Frankenstein are in a new attraction called, "Frankenstein's Castle". After Alvin drives a crazy bus ride, they miss their next performance and get locked in the park after closing time. Dr. Frankenstein figures that the castle isn't scary enough and re-creates the real Frankenstein and after the monster finds the boys, it starts a wild and wacky adventure!
As Alvin struggles with nightmares involving werewolves, the school play of Jekyll & Hyde is in jeopardy when the lead, Alvin, is suspended. In an attempt to boost his confidence, the drama teacher suggests Theodore, who's suddenly going through some canine changes.
The Chipmunks and the Chipettes go head to head in a hot air balloon race, and the winner gets $10,000. Unbeknownst to the participants, the "race" is actually a diamond smuggling ring!
Alvin learns the true meaning of Christmas.
A live-action/animated TV special featuring Alvin and the Chipmunks.
Donald flies his model airplane into Chip 'n Dale's tree. Dale climbs in and proceeds to cause trouble.
A short about what happens under and around us. A chipmunk and a small mouse go on an adventure; they grow and learn about life and its obstacles.
Enthralled with tales of the Great North Forest conveyed to him by friendly carrier pigeon Pippo, young chipmunk Glikko leaves the safety of his comfortable cage to explore the world. Stars Jim Backus and Orson Welles.
The Chipmunks head for outer space in this affectionate Star Trek spoof. Theodore stars as Dr. McRoy, who's abducted by aliens. Now it's Capt. Dirk (Alvin), Mr. Speck (Simon), Uhaha (Brittany) and the crew of the USS Boobyprize to the rescue. But will they reach McRoy before he's brainwashed by his captors? Two additional episodes from the beloved animated series, "Elementary, My Dear Simon" and "Chip Tracy," are included as a bonus.
Donald's playing lumberjack, but the targeted tree just happens to be the home of Chip 'n Dale. They give Donald plenty of trouble cutting down the tree, but eventually he succeeds. The wily chipmunks, though, manage to get their revenge on the homewrecker.
Hugo gets an audition script for a chipmunks ad and begins to have strange dreams centred around the mascot.