Alvin's Obsession is an episode of The Chipmunks series.
Alvin wishes to become the star of the new school musical so badly he puts up posters before he's even given the role. Unfortunately for him, the role is given to Apollo Jones. Theodore tries to get him to forget about the lost of the lead by telling him to sign up for a bake-off. Alvin jumps at the idea to regain his honor and prove he's the best. Once he loses again, Alvin sets out to prove is better than Apollo at something but still loses. Apollo takes his trophies home where he receives a call from Alvin challenging him in anything. During their "competition in anything," Alvin tries and tries to beat Apollo until he is forced to bed with full body injuries. Their last competition is in astronomy, which Apollo wins by circling the Earth in a rocket and traveling faster than the speed of light. When Alvin demands how he does it, Apollo reveals winning's all he has and Alvin is the real winner as he has a loving family, unlike himself.
- "Shakedown" originally performed by Bob Seger.
- This episode reveals that Alvin always wants to be the best.