While waiting for procrastinating Alvin on one of their dates, Brittany has a dream and becomes "Bratty Hayes" and Alvin becomes "David Alvinson", detective team. The plot revolves around Alvin trying to stop Brittany from marrying an evil villain - played by Simon.

Simon hosts his own show, playing Sherlock Holmes investigating several mysterious robberies.

The Chipmunks and Chipettes are in detention. They figure out together who could have knocked over the statue of Thomas Edison.

Alvin and Simon work together to help Theodore pass his American History test.

The Chipmunks go on a treasure hunt and meet the ancient Chipmunk tribe called the Twee-Twee Tribe.

After playing a video game, the TV blows up. Dave decides to distract the Chipmunks with the book Treasure Island.

This episode takes a look back at the history of the Chipmunks' career.

Alvin is forced to clean up the house after throwing a wild party while Dave is away and is not allowed to go with his brothers to Fantasy Park. During which, he combats his fear of loneliness, and experiences bizarre incidents including an alien.

The Chipettes are Alvie's Angels, a crime fighting team to hunt down the most popular jewel thief named Chazz Fleming.

Alvin enrolls himself and his brothers in cadet camp.

Alvin sees a psychologist to go over his issues with his family.

Dave meets a woman he really feels a strong connection with. At first the boys disagree, but finds she can get along with all of them. The only thing preventing this relationship to work is her own three boys clashing with the Chipmunks.

Brothers will fight every so often, but will they fight too much leading to each of the Chipmunks get their own separate rooms?

Dave is stuck at the studio all night to mix the boy's next album. But he leaves a Babysitter to after the Chipmunks while he's gone. After watching a detective movie, Alvin suspects her to be a murderer.

Alvin is desperate to try and buy a Trans-Go-Go Bot, but Dave and his brothers will not lend him the money to get it. He decides to do the grown-up thing and get a job at the zoo.

Alvin, Simon and Theodore find a huge attraction to one of Miss Miller's toys. Instead of asking her if they could keep it, they steal it from her attic. Dave tells them the beginning of a story, but chooses to let the boys come up with the conclusion.

As an experiment Dave tries his skill as a rock singer and becomes a success.

Alvin has a misunderstanding with a tough kid in his class, and ends up being challenged to a fight with him.

Vinny, the Chipmunks' mother, comes for a visit, but has difficulties adapting to the modern way of life.

Uncle "Adventure" Willy

Micky, a new Irish boy at school, claims that he has his very own leprechaun. The Chipmunks are keen to investigate.

Theodore develops a crush on a girl in his class named Juliet. Wanting some expert advice, Theodore asks Alvin for his help. Unwillingly, Alvin says a romantic line that Juliet overhears and she ends up developing a crush on Alvin instead of Theodore.

Brittany tries out for Alvin's football team. To get even, Alvin joins her cheerleading squad. Will they set aside their differences and help each other succeed?

The Chipmunks go to Berlin to play in the "Wall of Iron" concert by the Berlin Wall. There they meet and befriend a young girl named Caterina whom has a brother named Eric that lives on the other side.

A crook uses the Chipmunks tour as camouflage for his own evil deeds: While people is out watching the Chipmunks concerts, his trained chimpanzees raid the empty houses.

Alvin plays one prank on Theodore and gets him to eat a dog biscuit. To get even, Theodore, with Simon's help, plays a trick on Alvin and makes him think that his younger brother is actually turning into a were-dog.

Miss Miller is invited to go to her High School reunion. But without her boyfriend to go with, the Chipettes try to get one of the Chipmunks to dress up to be Miss Miller's date.

By a fluke, Alvin actually passes his math test whereas, Simon mysteriously fails. Afterwards, Alvin believes he is psychic, and so does everyone else, except Simon.

Alvin is upset that he can’t seem to keep up with the rest of his track race team. Being that so, his coach decides to let him become a trainer for one of the athletes of the Special Olympics.

Alvin is upset that there is a new boy that just happens to be better at everything. To prove that Alvin has what it takes to beat this kid, he challenges him to anything he can think of.

Dave is feeling depressed and is thinking that the Chipmunks would do better if he had never been apart of his life. Will the spirits of the Chipmunks convince him that he is indeed been an impact on Alvin, Simon, and Theodore’s lives?