Mrs. Frumpington, the head of a group called The Ladies of the Square, visit the Seville House. She explains that the goal of the group is to ban certain miserable music on television and radio. After she expresses the group's desire to outlaw Chipmunk music with the support of 2,500 signatures, The Chipmunks devise a plan to stop her. To do so, Alvin stops by her house and the boys cause her to become joyous to their music until she's trucked away to Happydale: The Home For Tilted People.
While Dave and the Chipmunks are walking down the street they stumble upon a car dealer kicking an ostrich, who is trying to hatch a egg-shaped car, out to the street. After Dave refuses to do anything to help her, Alvin and the dealer trick Dave into "autographing" a contract, resulting in him taking ownership of the car along with the ostrich. Once Dave's frustration hits the breaking point, he grounds the boys from watching television until they get rid of the ostrich. The episode ends with the car "hatching" seven chicks.
The narrator introduces the Sevilles to the audience and informs us that neighbors are constantly moving out with one moving in only occasionally. While Dave is at the store, The Chipmunks meet the new neighbor, who does not like being disturbed as he sleeps. The neighbors are involved in multiple conflicts until Alvin blasts him into space to orbit the moon.
While vacationing at a beach resort named Surf, Sand and Sea View, Simon, Theodore, and Dave enjoy the scenery as Alvin watches TV, uninterested in the beach. When Alvin is accidentally hit with a beach-ball by the girl next door, he is taken by her so much that he literally floats. Dave and his brothers believe he is really sick when he takes a shower and skips lunch. When Alvin finds out she is on the beach he sets out to impress her with various maneuvers: back-flips, trampoline tricks, and surfing. After she realizes he is "Alvin the Chipmunk," her favorite singer...
Unwilling to do his chores or to rehearse their new song, Alvin is encouraged by his evil alter-ego to seek out the team's agent and work as a solo act. The evil conscience tells the boy of his future successes without the team. Then his good alter-ego points out how his father and brothers will struggle without him. Learning his lesson, Alvin returns home and he practices the new song and later cleans up the house.
The boys are tired of being stuck in the house and they convince Dave to take them out by showing him a brochure with beautiful pictures for Valhalla Estates. Dave calls Sam Valiant, now a real estate agent, who tries to sell David Seville and the boys a rundown piece of property. They are later saved by a tribe of politically incorrect Indians who actually own the land.
When Dave and the boys go to a national park for their camping trip, they accidentally camp under a waterfall, convincing Dave it's raining. They move the tent (which happens to be over a geyser). When it erupts, Dave blames Alvin. Later, when a bear takes Alvin's cap, Dave thinks the bear ate Alvin (who's out digging gold) and runs to the police. The man tells Dave there's a bandit out in the woods, quickening Dave's resolve to find Alvin. Alvin and the bear find the loot and capture the bandit. Afterward, the park ranger takes Dave away since he thinks Dave's crazy.
Dave comes home from work to find the yard and the house a mess. Disappointed in the boys lack of personal responsibility, Dave decides to begin acting as a drill sergeant to get The Chipmunks' acts straight. Unhappy with having to do work, Alvin and his brothers conspire to get back at him by contacting a news reporter and trying to show her that Dave is a slave driver only to have their plan backfire.
Dave and the boys head for a popular dude ranch out west for a vacation. Once they get to their hotel, they discover that Sam Valiant is the room clerk. Hearing that Dave is attempting to create a western song, Valiant keeps pestering Dave to use one of the songs he's written and replace The Chipmunks with himself by using various disguises. Unable to stand him any longer, they quickly pack up and leave. Valiant finally finds himself a partner out in the desert.
While out in the jungles of Africa to record animals sounds for their new record, they hear a new and mysterious sound. While trying to find the source of the sound, Dave discovers are being stalked by a native with what appears to be a deadly blow gun filled with poisoned darts. After they jump into a cauldron and hear "Witch Doctor" playing, they are relieved to hear that the native is not dangerous, but is a fan who wants to play his flute for them.
Alvin meets his new neighbor Bentley Van Rolls III, who turns out to be a spoiled little rich kid. Bentley has his butler, Reese, spy on Alvin from their balcony before heading out to attempt to play with Alvin. Instead of having fun himself, Bentley has his butler play his music and toys for him. Tired of being bored by his things, he sets out alone to learn how to have fun. It's not until Bentley saves Alvin from being hit by a car that he decides to show the kid how to have fun by tricking him into doing his chores.
After The Chipmunks disrupt a visit with Mrs. Frumpington by breaking a window and acting sarcastically, Dave loses his temper. Mrs. Frumpington volunteers to teach the boys good manners. She attempts to instruct the boys on how to properly act at the table and how to treat visitors. The Chipmunks use the lessons to take advantage of Dave by buying over $100 worth of junk from a seller, R. B. Huston, and by making Dave buy them enough groceries to stay in their tree platform for a few days.
Alvin tries to play baseball with his team and care for a bratty baby, Billy Brown, at the same time. While Alvin is playing, Billy keeps bugging Alvin to let him play ball, but Alvin won't let him since he is too young. When his team is losing "with the bases loaded", Alvin has the infant play against the rival team's lead player Roger. The little guy, given the nickname "slugger", hits a home run and wins for Alvin's team.
Chuck Wagon, one of Dave's cousins, comes to visit. After he states he can't do anything, Alvin makes it a point to teach him to do everything. The boys try to find something Chuck can do, but are unsuccessful. Disappointed in himself, Chuck begins to sing country tunes and play the guitar. Excited Chuck can do something, Dave and the boys help their cousin launch a recording career. When the news spreads, every hillbilly relative of Dave comes looking for his help in making them successful too.
Dave and The Chipmunks have just completed a very busy schedule and are looking forward to a peaceful cruise. While aboard the ocean liner, Alvin, who only wants to sleep, is constantly being annoyed by an obnoxious social director named Roger Marsell at every turn. Alvin finally gets back at the pest by having him step into a lifeboat and sending him into the sea.
The Chipmunks are concerned by Dave's unusually behavior and attempt to follow him. Once they stop in front of the Justice of the Peace, they believe Dave's getting married. Back home they overhear Dave on the phone and believe the woman soon to visit is his fiance. The boys spy on their conversation and become convinced Dave will get rid of them. When they confront Dave they find out she is really a representative for Sam Sweetheart's Swimming Pools Construction Company who is helping Seville pick out a swimming pool.
Stanley the Eagle finds a lost necklace and gives it to an eagle statue atop a clock tower. (Stanley thinks that the eagle statue is a female, and he wants to impress her.) Unfortunately for Stanley, the owner of the necklace reports her jewelry stolen and Stanley is being sought by the police. Alvin and his brothers find Stanley and take him to the cops. They drop the charges, but the cops force Dave to be responsible for Stanley.
Theodore finds a dog (Alexander) at an animal shelter and drags him home. Theodore tries to convince Dave to allow a dog to live with them, but he says no since they travel too much. Desperately wanting a dog, Theodore hides Alexander in the basement; when he escapes, Dave believes there are burglars and he calls the police. Dave becomes angry when he finds Theodore's been hiding the dog, but his brothers convince Dave to take him on their trip.
Dave inherits the Chesley Estate and is excited to show the boys. Unknown to Dave, a ghost (JP Lester) is excited to have the opportunity to scare him in order to get the Ghost of the Year award. After the ghost's first failed attempt, Dave has Simon bring the things in from the car and Theodore starts painting while Alvin sets off looking for ghost tracks. The ghost fails three more times at scaring the boys. After failing yet again (mistaken for Alvin), the ghost sleeps with them. In the morning, they find out he is a ghost and take off running. When the ghost ...
Dave's ready to rehearse a new song but the boys aren't (Alvin's playing with a yo-yo, Simon's reading, and Theodore's playing with a parakeet (George)). When Dave walks out on his boys (to play golf) following a heated argument about their new song, Alvin takes over and he tries to have his brothers perform a different song. In doing so, he begins to sound like Dave. After some time arguing with each other and the neighbor about how to yell Alvin, a large group of people congregate outside the house. Dave arrives to the pleasure of the boys and they sing his song.
The Chipmunks have just got back home from a long performance tour. While Dave, Simon, and Theodore are cleaning up the house, Alvin tends to his garden only to get into a match with the neighbor's dog who keeps burying its bone in his garden. Even after talking to the neighbor, the dog keeps harassing Alvin and his garden. Tried of dealing with the dog, Alvin rushes to get a whistle after Simon reads him part of Dog's Life. It's not long before he realizes the whistle's side effect.