Bobby is a friend and classmate of Max's. He appears to have a surfer bum appearance, as he is usually seen in a T-shirt, shorts, sandals, and sunglasses. He also had an orange mohawk in A Goofy Movie and a orange buzz cut in An Extremely Goofy Movie. It seems he uses his A/V connections to do favors for other students, as he mentions a required fee to help Max. Bobby is also known for his obsession with canned processed cheese, and he will eat it directly from the can.
In A Goofy Movie, he is apparently one of the Audio/Visual students. In exchange for a fee, a can of Cheddar Whiz, he helps Max and P.J. to hijack the auditorium stage during Principal Mazur's end of school speech. While Max performs, and P.J films, Bobby handles the technical aspects, which include getting rid of the Principal and lowering a giant screen, where the film plays. Later, Max trips over a cord, and ends up on stage. Max continues his performance, and Bobby uses a fire extinguisher to create a smoke effect. However, the boys are caught by Mazur, and are sent to his office. Bobby is the second of the boys to be called into the office, but it is unknown what punishment he was given.
At the end of the film, he is one of the guests at an end of school party hosted by Stacey, the student body president. There, Bobby watches Max and Goofy dance onstage with Powerline. At one point he gets into a Cheddar Whiz fight with Stacey, and when the two reach for the can, they suddenly notice each other, and it is hinted that they have fallen for each other.
In the sequel, Bobby has a larger role as Max's friend and College X-Games teammate. Now 18 years old, Bobby starts to attend college with Max and P.J. The three plan to compete in the upcoming college X-Games. The three are able to get past qualifying, but in the semi-finals, they lose P.J. to a stunt pulled by a competing team, the Gammas. Bobby and Max are almost disqualified for not having enough members, but Max convinces Goofy to join at the last minute. Bobby is taken out of competition when a Gamma sabotages his bike and makes him crash. In the end, Bobby's team wins thanks to Max, Goofy, and Tank.
- Bobby, along with PJ, are notably the only characters to not appear on House of Mouse.
- In An Extremely Goofy Movie, Bobby makes a reference to his actor, Pauly Shore when he says "Bu-Udy".
- In An Extremely Goofy Movie, Bobby's outfit for most of the movie is almost identical to that of Shaggy Rogers from the Hanna Barbera cartoon franchise Scooby-Doo.
- In An Extremely Goofy Movie, Bobby doesn't have his can of Cheddar Whiz.
- Bobby's hair style changed between A Goofy Movie and An Extremely Goofy Movie, going from a more hairy orange mohawk to a buzz cut.
- Bobby has many similar aspects to a Stoner. Coincidentally, Pauly Shore portrayed a character with a similar name, Stoney in Encino Man.
- Bobby is seemingly the first Disney character to question why him and some of the others wear gloves, shown in An Extremely Goofy Movie. The answer to this is that Walt Disney didn't want Mickey Mouse to have claws, since he thought it would scare children. He therefore, after drawing Mickey with simple black hands, started to draw him with white gloves, then gave that look to some other characters too.