Alvin faces a dilemma when he's offered $500 or a mystery prize. The Chipmunks and Chipettes use Simon's time machine to explore the outcomes of his choice, revealing a life of luxury if he takes the cash and poverty and a lost singing voice if he chooses the mystery prize.
1. Back to Dave's Future/Tell It to the Judge
Aired: Sep 12, 1987The Chipmunks' time-traveling adventure takes an unexpected turn as they enco...
2. Sincerely Theodore/My Pharaoh Lady
Aired: Sep 12, 1987Theodore's journey to find love leads to a dramatic transformation as he emba...
3. Simon Says/When the Chips Are Down
Aired: Sep 19, 1987A mysterious robbery sets off a thrilling treasure hunt among the friends, bu...
4. Alvin, Alvin, Alvin!/Dave's Dream Cabin
Aired: Sep 19, 1987Alvin's self-esteem takes a hit when he feels overlooked, prompting him to dr...
5. Old Friends/The Mystery of Seville Manor
Aired: Sep 26, 1987The next episode descends into darkness as the characters venture into the an...
6. Ask Alvin/Theodore Lucks Out
Aired: Sep 26, 1987Alvin starts an advice column, sharing his wisdom with those around him, whil...
Aired: Oct 3, 1987Simon's ingenuity is put to the test as he constructs a machine that enables ...
8. Just One of the Girls/Goin' Down to Dixie
Aired: Oct 3, 1987In the next episode, the Chipettes abandon their luxurious Hollywood aspirati...
Aired: Oct 10, 1987Alvin's reckless skateboarding nearly causes chaos when he barely avoids hitt...
10. The Secret of Seville Manor
Aired: Oct 10, 1987The Chipmunks set out on an adventure to Seville Manor in England, searching ...
Aired: Oct 17, 1987Alvin's relentless advice-giving reaches a boiling point, prompting his sibli...
Aired: Oct 17, 1987Theodore's track and field performance experiences a stunning transformation ...
Aired: Oct 24, 1987Alvin faces a dilemma when he's offered $500 or a mystery prize. The Chipmunk...
Aired: Oct 24, 1987The Alvin and the Chipmunks gang set sail on the Island Lady cruise ship, exp...
Aired: Oct 31, 1987In the next episode, the Chipettes and The Thrillers find themselves in the m...
Aired: Oct 31, 1987The Chipettes are thrilled to perform at the iconic River Ritz Hotel in New O...
Main Cast
