|In their third year at Greendale, Troy and Abed decide to move in together. They invite the study group to their new apartment for a house warming party and order food for the event from Pizza Time Pizza. It is Toby that delivers their pies to them, unaware that six different timelines are unfolding, and in one of them, he might find true love. His first appearance was in the Season Three episode "Remedial Chaos Theory". He makes a brief cameo in the episode "Course Listing Unavailable". He is portrayed by musician/actor Robert Tarpinian.|
Toby plays an important role in the six timelines unfolding differently from the "Prime" timeline. His arrival forces one member of the study group to leave Troy and Abed's apartment to go meet him. When Jeff rolls a die and selects a particular member to leave, six alternate scenarios occur based on who is absent from the housewarming party. His most significant encounter occurs in the timeline where he meets Britta. She quickly falls for him, and they immediately become engaged. She brings him upstairs to announce their involvement to the others, but it's overshadowed by the drama that went down between Troy and Pierce ("Remedial Chaos Theory").
|He makes a return appearance later in the year in delivering pizza to Troy and Abed's apartment again. Britta volunteers to answer the door, and an echo of her timeline from Remedial Chaos Theory" occurs. Feeling depressed about her and the study group's expulsion from Greendale and due to her tendency to fall for the wrong guy, she finds herself smitten with Toby. Troy then calls out to Britta and compliments her, telling her that she is not the worst. No longer feeling bad about herself, she grabs the pizza from Toby and slams the door in his face. Having overheard Abed talk about his theories, Toby loudly asks what he meant by different timelines ("Course Listing Unavailable").
It is worth noting that in his second appearance, Toby is actually able to go upstairs to Troy and Abed's apartment to deliver the pizza when he originally had to wait for someone to come downstairs to get it from him. Also, the name "Toby" was used twice before the pizza delivery guy. In the Season One episode "Advanced Criminal Law", Señor Chang threatens to fail his class except for a student named Toby; he then strokes Toby's cheek affectionately. In the Season Two episode "Accounting for Lawyers", it's revealed that Jeff's middle name is "Tobias" which is the formal version of Toby. In Season Four, Abed becomes friends with a fellow Inspector Spacetime fan named Toby.
In Season One, two other unnamed pizza delivery guys were prominently featured on the show. The first pizza guy was in "Communication Studies"; he delivers a pizza to Jeff and Abed during their drunk dial session to Britta. He ends up taking part in Jeff and Abed's drunk shenanigans in an homage to "The Breakfast Club". The other one was in an end tag in the episode "The Art of Discourse". Troy and Abed are playing a game to figure out what their porn names would be. Following the cliche porn trope, a pizza delivery guy shows up and starts making double entendres about the pizza someone ordered.
In the Community: The Complete Third Season DVD commentaries it's mentioned a few times by creator Dan Harmon that actor Jason Biggs from the "American Pie" franchise was asked to play Toby but passed on the cameo. The character, as originally intended, was meant to be an actor researching his role as a pizza delivery guy by pretending to be one.