Erik Miner takes a look back at the history of The Chipmunks' career by using flashbacks to past episodes.
- The Victrola Awards
- Big Dreams - Simon used his time machine to view The Chipmunks and The Chipettes' futures to determine if Alvin should take the $500 in cash or a mystery prize.
A mother of two small children states that she used to love playing The Chipmunks' music as a kid, but now she is forced to listen to them over and over and over again. As her kids are throwing food, she states that Theodore was her favorite since 1) he ate his food and 2) he is sweet like the time he saved Clarence.
- How You Gonna Keep 'Em Down on the Farm? - After Theodore learns the fate of the winning cow, he and Clarence run away. On their way out of the country, Theodore stumbles into a robbery and is mistaken as the thief. Lucky they are spotted by the police and the situation is cleared up.
A construction worker states that Alvin is his favorite because he has all the cool moves. He laughs at the times Alvin is out of control like the day he had a bunch of dancing camels.
- Don't Be a Vidiot - Alvin is directing a music video but can't get everything into the shot. He decides to back up only to hit a wall and collapse the entire building.
Erik Miner, the narrator, explains the audience needs to go to The Chipmunks' musical roots - a small cottage.
- The Chipmunks Story - The Chipmunks, as infants, perform their first single.
David Seville explains that their success paved the way for many singing animal groups such as The Turtles and Three Dog Night. The quick rise of The Chipmunks led to multiple commercial endorsements such as Poopsie Cola and Chipmunk Jeans.
- Alvin's Oldest Fan - Alvin holds a contest that generates mountains of letters leading Theodore to state "Do you think all this attention will go to Alvin's head?"
Alvin did just that when he caused a cartoon uproar by stating "we're more popular than Mickey Mouse," decreasing their fan base. Apparently it did a number on him.
- Alvin, Alvin, Alvin! - While Alvin is depressed on a rocking horse in the attic, his brothers try to cheer him up with a cake and some books.
Bad career moves had The Chipmunks on the brink of extinction.
- Maids in Japan - The Chipmunks perform in a Kabuki Theater while dressed as maids.
- The Chip-Punks - Alvin attempts to convince his brothers that they need to change the band's image to help pick up the big performances.
Alvin begins to state he maintains a bit of class at all times, but Simon corrects him by stating he would do anything to sell tickets.
- Alvin on Ice - The Chipmunks perform a honeybee routine on ice, crashing the show.
Alvin claims they were going through an identity crisis, but Theodore correct him this time.
- Alvin, Alvin, Alvin! - Alvin tries out a new personality in which he is Michael who has a llama.
Seeing as their careers were struggling, The Chipmunks pursued other endeavors.
- A Horse, of Course - Alvin enters himself (the rider) and his brothers (the horse) into the Kentucky Derby.
- My Fair Chipette - The boys beautify up Jeanette only to send her flying down the stairs.
As a comeback, Alvin decided to start performing to small crowds with Simon emphasizing small.
- A Rash of Babies - While babysitting a large group of infants, Alvin attempts to find a song they will like.
This experience introduced The Chipmunks to a new generation of fans and the music video. Their video for "Bad to the Bone" pulled them back to the top. When ask about their influence, Simon and Theodore quickly cover Alvin's mouth when he attempts to state they are better than someone else.
- "Puttin' on the Ritz" - Don't Be a Vidiot
- "Witch Doctor" - The Chipmunks Story
- "Poopsie Cola" (a "Witch Doctor" parody/remix)
- "Three Little Maids From School" - Maids in Japan
- "Bad to the Bone" - Alvin's Oldest Fan
- The context of many of the clip episodes is used incorrectly for this interview.
- Alvin causes an uproar by stating that The Chipmunks are "more popular than Mickey Mouse". This is a spoof of John Lennon's controversial "Bigger than Jesus" remark.
- This episode is the first of only two episodes to be comprised primarily of clips from past episodes; the other being Alvin in Analysis.
- This episode was produced by Murakami-Wolf-Swenson.
- This was the second of six episodes to premiere in syndication.