He is played by Zachary Levi.
He also lives with Aunt Jackie. The Chipmunks refer to her as "Popcorn Jackie" and he refers to himself as the Tobester.
In the events of the second film Dave is seriously injured in a benefit concert as a result of Alvin being carried away and knocking a giant Alvin billboard into Dave, sending him flying a good distance. Dave survives the accident but is left temporarily disabled as of the result. During his recovery Dave reveals that he has arranged for them to go to school and for popcorn jackie to watch after him during his recovery. When Toby arrives to take care of the chipmunks he is depicted as being lazy and having a love for video games as well as having a sarcastic demeanor. It is hinted through movie clips that Toby is having trouble controlling them and is often quarreling with the chipmunk trio as an example while playing Wii Bowling. Alvin breaks Daves new T.V and a nervous Alvin suggests they play his second favorite game which is to hide the broken TV much to the shock and disbelief of a stunned Toby also he is referred as "Taco Boy" by Simon and when Toby claimed as being extremely popular when he went to school he is countered by the disheveling chipmunks who point out that he is still living with his mother, refers to himself as the Tobster and constantly going "pew, pew pew". A slightly amused Toby responds by giggling sarcastically and sending them off to bed early. It has also been revealed that Theodore is constantly trying to bond with his temporary guardian but after failing runs away from home.
Later on, Toby, Alvin and Simon find Theodore at the L.A. Zoo. Theodore escapes from being eaten by an eagle. Near the climax of the movie, Toby is able to stall Alvin's income to bring the Chipettes to the Music Festival by singing to his crush with a few lines. Despite not singing much, the audience critically accept what he says into the microphone and Alvin managed to get in time with the helicopter and the Chipettes after Toby's unplanned talent.
Alvin and the Chipmunks : Chipwrecked
It is highly unlikely Toby will be in this, though this may not be confirmed,yet.
- He was tormented by bullies when he was a teenager at the same school the Chipmunks go to in the Squeakquel. He had his face dumped into the toilet and was pinched by people because of a paper that said "Pinch Me" taped to the back of his shirt which he didn't notice.
- Toby is portrayed as an "Alvin Super Fan" on the Alvin and the Chipmunks:The Squeakquel bonus features "Squeak Along" DVD. Whenever he is being shown talking, his name appears at the bottom of the screen with an animated Alvin and "Alvin Super Fan" tagged along behind it. Toby doesn't mention that he is an Alvin fan in the sequel at all.