May the Best Chipmunk Win is an episode of the Alvin and the Chipmunks series.
When The Chipettes move to The Chipmunks' school, the boys give the girls advice. Alvin advised Brittany to do something 'big' as Brittany said she wanted to fit in school fast, so then taking Alvin's advice, she runs for school president, not knowing that Alvin is running for school president as well. Brittany is shocked when she discovers she is running against Alvin and even more surprised that she cut Alvin's lead so fast. After the final poll is revealed, they discover that Jeanette has the deciding vote. Both Alvin and Brittany try to influence Jeanette's vote with gifts and kind words. She ultimately chooses Alvin because he is more qualified, which makes Brittany upset. Alvin makes The Chipettes a welcoming party so they can all celebrate together.
- "It's My Party" originally performed by Lesley Gore.
- "Celebration" originally performed by Kool & The Gang.
- This is the second appearance of The Chipettes.
- The Chipettes become main characters as of this episode.
- This is the first episode not to feature David Seville.
- According to the first song, Brittany is older than Jeanette.
- The Chipmunks use the donkey while The Chipettes use the elephant in their campaigns. The donkey is the symbol of the U.S. Democratic Party while the elephant is the symbol of the U.S. Republican Party.
- Part of The Chipettes and The Chipette Diaries DVDs.