Biography
Simon is the tallest and the middle brother of the Chipmunks (the oldest in CGI series), usually singing low harmony. In addition to having substantial book smarts, Simon possesses a dry sense of humor and a keen wit. He wears glasses and blue attire and has blue eyes (a trait he shares with Alvin). Simon is an enthusiastic scientist, with his own laboratory in the basement of the Chipmunks' house, and is known to read classical literature as well as science texts. Simon is kind, gentle, logical, responsible, and at times poetic, and often takes charge when Alvin goes too far with his harebrained schemes. Although Simon tends to disagree and argue with Alvin, he truly loves his brother and sticks by him despite everything. Simon tends to hold grudges, but these are often short-lived as he knows that he should be more forgiving. Simon plays the bass, bass clarinet, saxophone, bagpipes, tuba, and drums, among others. In vocal harmonies, he consistently sings the lower parts due to having a deeper voice than his brothers. He is shown playing the keyboard in the original open for the 1980s series.[citation needed] He was also shown playing guitar in a 1980s Hardee's commercial.
Simon is often implied to have a crush on Jeanette, as she is like him in many details: wearing glasses and blue or purple attire and having a high IQ, possibly rivaling his own. However, he seems braver in standing up to siblings than her because Jeanette does not often stand up for herself when Brittany pushes her around. But like Simon to Alvin, Jeanette shares a sisterly bond with Brittany. Simon and Jeanette are rather shy around each other and are not very open with their feelings, but Simon does display physical affection for Jeanette, including catching her when she falls, holding her hand, and giving her hugs.
Like his brothers, Simon was originally voiced by Ross Bagdasarian Sr. In the animated series and film, he was voiced by Ross Bagdasarian Jr. Matthew Gray Gubler voiced Simon in the live-action/animated film series.