This DVD's six episodes start off with the Chipette's first day at Alvin and the gang's school, and the female trio show up just in time for the race for school president. So what better way to make lots of friends and have people get to know you than to run (at least that's what Brittany thinks). What she doesn't realize is that she is running against Alvin (who was unopposed before she appeared). Of course, this kicks off a heated political campaign with more than its fair share of smearing.
After that, "Operation Theodore" has the Chipettes working as nurses in a hospital. When Brittany loses one of her patients who is about to have his tonsils removed, she asks Theodore to stay in his bed while she finds him. Well, before she returns, the doctors show up and cart Theodore away to prep for the operation. So, of course, the three girls and the other two boys must race around the hospital looking for both Theodore and the missing patient.
"Sisters" once again focuses on Brittany as she has the chance to get into a very snooty clique at school, provided they find her "special" enough. As she tries to impress her possible new friends, she ignores her own sisters more and more, especially Jeanette who has partnered with her in a science experiment. Things come to a head shortly after the girls from school decide to have dinner at the Chipette's house and expect to see both a maid and a butler.
In "The Greatest Show-Offs On Earth," the six chipmunks work together to help a circus from their childhood as it struggles to make the necessary mortgage payments, while "My Fair Chipette" has Alvin betting he can turn anyone into a beauty pageant winner. Of course, he has his work cut out for him when brainy Jeanette is chosen as his contestant.
The final episode on the disc is "Tell It To The Judge" where Dave leaves town for a trip to New York City and Alvin decides to take Dave's new bike out for a spin. But when he runs into Brittany and ruins the bike, he takes her to TV's Public Court to get properly compensated (so that he can get a new bike before Dave returns). As always with this show, things get out of hand and their secret will get out.
Much like the rest of the series, these episodes feature one or two song covers that are very 80's. Song's like "Girls Just Want To Have Fun", "It's My Party" and "Material Girl" are just a few of the covers song in the character's high-pitched voices. Both the Chipmunks and the Chipettes are staples of 80's cartoons and anyone who grew up during this era should love the chance to see these classic cartoons again. While the songs themselves date the series, the show itself stands the test of time and should even be enjoyed by the current generation of kids.