In Alvin and The Chipmunks, Simon’s voice is that of Matthew Gray Gubler. Simon is the intelligent chipmunk that wears a blue sweatshirt and glasses. He is not the funniest chipmunk, but he sure does know how to play chess! Simon is always the one that is thinking ahead of time and tries to come up with the best solutions. Simon is more dramatic than the other two chipmunks because he thinks everything has to go perfectly. He can play the bass, saxophone, tuba, and drums. Deep down Simon loves Alvin, but he still worries that they share the same gene pool.