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Season guide

Alvin and the Chipmunks: Season 5

16 episodes Premiered Sep 12, 1987 Updated Oct 2, 2026
Previously on Alvin and the Chipmunks

Season 5 Lore Primer

Key plot threads, lore context, and character stakes you need to remember before diving into this season.

  • ⚡ Directly follows the overarching narrative developments of Alvin and the Chipmunks Season 4.
  • ⚡ Faction dynamics and core character alliances shift under escalating external stakes.
  • ⚡ Crucial mysteries introduced previously reach key turning points and narrative reckonings.
  • ⚡ Sets up serialized story arcs that build directly toward the climactic season finale.
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Season 5 Episodes

Episode Guide

🛡️ SPOILER SHIELD

Season 5 Progress Shield

Future titles & synopses blurred. Tap "Reveal" on any card to peek.
Binge Efficiency Engine

Season 5: Filler vs. Essential Canon

Filter episodes by narrative weight. Focus on essential mytharc and skip standalone side quests.

19%
81%
Mytharc (3): Crucial lore & season climaxes
Core (13): Character development & subplots
Side Quest (0): Standalone / filler
S5·E1 Mytharc

Back To Dave's Future

Sep 12, 1987 · 30 min

A wild ride on a merry-go-round sends the Chipmunks back to 1962. They meet a younger Dave. Without the boys' help in winning a band contest, he will spend his life as an accountan

S5·E2 Core

Tell It To the Judge

Sep 12, 1987 · 30 min

Alvin "borrows" Dave's new bike, and while he is out riding he accidentally hits Brittany who is out roller skating. The bike is ruined, and something is wrong with her skates. The

S5·E3 Core

Sincerely Theodore

Sep 19, 1987 · 30 min

Theodore goes on a diet so he could go on a date with a pen pal, who is also one of Alvin's biggest fans. Things go wrong when Alvin finds out that Theodore's date is actually the

S5·E4 Core

My Pharaoh Lady

Sep 19, 1987 · 30 min

Brittany makes a bet with Missy Snootson, another girl in her class, that if the mummy of king Rooten Tooten does not rise from the dead and go to her home by midnight, Brittany mu

S5·E5 Core

Simon Says

Sep 26, 1987 · 30 min

While Dave is out of town, Miss Miller babysits the boys and they go to a movie about killer space squids attacking the earth. Accidentally miss Miller breaks Simon's glasses. When

S5·E6 Core

When the Chips Are Down

Sep 26, 1987 · 30 min

The boys have to paint the garage after they got spray paint on the walls while repainting their bicycles. Simon and Theodore feels bad because they always have problems with Alvin

S5·E7 Core

Alvin, Alvin, Alvin!

Oct 3, 1987 · 30 min

Alvin goes through an identity crisis and starts trying all kinds of different personalities, with embarrassing results.

S5·E8 Core

Dave's Dream Cabin

Oct 3, 1987 · 30 min

After years of scrimping and saving, Dave is finally able to afford their own vacation cabin. Alvin hears that Robby Leach, the host of the show “Lifestyles of the Truly Fabulous”

S5·E9 Core

Old Friends

Oct 10, 1987 · 30 min

Alvin nearly runs over an elderly woman in the mall with his skateboard. When Alvin finds out that she is wealthy, he sends out invitations for a senior citizens' party in order to

S5·E10 Core

The Mystery of Seville Manor

Oct 10, 1987 · 30 min

While in England, the Chipmunks check out Seville Manor to investigate if they have any relation to the man who owned it.

S5·E11 Core

Ask Alvin

Oct 17, 1987 · 30 min

The family becomes fed up with Alvin, who always gives out advice whether it is wanted or not. So Simon and Theodore get Alvin to become the new host on the talk show “Mr. Advice”

S5·E12 Core

Theodore Lucks Out

Oct 17, 1987 · 30 min

Theodore is feeling unlucky in the track and field. He finds a bent out of shape dime and his luck changes.

S5·E13 Core

Big Dreams

Oct 24, 1987 · 30 min

Alvin gets a registered letter from the Publishing Warehouse stating he's a winner! He either could take $500 or the mystery prize, but had to call by 6:00 pm to decide. So with

S5·E14 Core

Island Fever

Oct 24, 1987 · 30 min

The Chipmunks and Chipettes get to perform on a high class cruise ship, the Island Lady, but instead they end up ship wrecked on an island.

S5·E15 Mytharc

Just One of the Girls

Oct 31, 1987 · 30 min

Miss Miller & the Chipettes are vacationing in Hollywood, as well as Miss Miller reuniting with her girl singing group, The Thrillers. In the lobby of the hotel, they learn that s

S5·E16 Mytharc

Goin' Down To Dixie

Oct 31, 1987 · 30 min

The Chipettes get an opportunity to star on the River Ritz Hotel in New Orleans, Louisiana.

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