- "I keep imagining myself in charge of a large empire."
- — Gary
Gary is slightly taller than Jimmy, but a bit more slender. He has brown hair in a low fade style with a part on the left, brown eyes, and has a notable scar over his right eye. He wears a teal Bullworth sweater vest, unique to him, over a grey shirt, and grey school slacks. He has a silver watch on his left wrist, and a brown leather wristband on his right. At Halloween he wears a Nazi Officer costume and carries a riding crop which Jimmy can wrestle off him. In the winter, Gary rolls his sleeves down and adds a navy blue winter hat with a black stripe to his usual outfit.
Gary has a very bad reputation among the other students and even staff in school. He is described by Algie as a sociopath, Pinky claims that he likes to torture people, and Mr. Galloway claims in Chapter 5 conversational dialogue that he saw Gary in the staff office and that "he can't be up to any good". Gary admits that he suffers from ADD, and also shows traits of narcissism and paranoia, often imagining he's in charge a large empire. He was on behavior medication but stopped taking it some time around Halloween, which is also what leads to his betrayal of Jimmy and Petey. He has also been a therapy patient of Dr. Bambillo. Despite being mentally unstable, he is highly observant, telling Jimmy that "nothing escapes his notice". However, he also thinks that friends are for the weak, seeing most people as tools to be used or enemies to be crushed. He tends to call people "friend", regardless of whether he's being friendly or hostile towards them. His insult of choice is "scum". Gary proves himself to be incredibly manipulative, to other students and adults, and highly intelligent, something he constantly reminds others of due to his arrogance and vanity.
His background is mostly unknown. He cites his parents as one of his "problems". Miss Abby speaks poorly of Gary's mother, and Mr. Smith is suggested to be Gary's grandfather since he shares the same surname and complains about the state of the family. Donald Anderson can be heard to mention that Mr. Smith (referencing either Gary's father or Grandfather) was kicked out of Bullworth Academy and went to prison. If this were true in reference to Gary's father, it could help explain Gary's behavior. Towards the end of the game, several townsfolk make comments about Gary's bad behavior and unstable personality.
Gary is very open about his plan to take over Bullworth, going so far as to shout that he intends to run the school in front of the clique leaders and their bodyguards during Russell in the Hole. Somehow, he was apparently able to convince them all to trust him, although most, if not all of his interactions with them took place off screen.
Role in game
Gary and Jimmy Hopkins become friends in the mission Welcome to Bullworth, with Gary introducing Jimmy to the school and the four cliques in the school. Gary tells Jimmy of his plan to take over the school and the two, occasionally with Pete Kowalski work together (although Gary frequently bullies Pete, and Jimmy has no desire to run Bullworth). However, Gary stops taking his medication and becomes increasingly paranoid, believing that Jimmy is plotting against him. Gary then leads Jimmy into a trap, forcing Jimmy to fight Russell Northrop at the end of Chapter One. However, when Jimmy prevails, Gary disappears into the background, creating trouble for Jimmy.
Gary first convinces the Preppies to turn against Jimmy, claiming that Jimmy said that Tad Spencer was inbred in The Eggs. He appears again in Chapter 3, helping Johnny and his gang in Wrong Part of Town. Gary then again disappears into the background, but also turns the Nerds against Jimmy, telling Earnest Jones (Nerd leader) that the pair could take over the school. After Jimmy defeats the Nerds, Gary turns the Townies against him and convinces them to start an open war against the Bullworth population. Jimmy then also loses control of the four school cliques and is expelled by Dr. Crabblesnitch, who was informed by Gary that Jimmy marked the Town Hall. While Jimmy is fighting the Townies, Gary becomes Head Boy at Bullworth, and manages to start a riot on the school campus, with the four cliques openly attacking each other.
Jimmy, Russell and the Townies manage to take control of the school again by defeating the clique leaders. Jimmy and Gary meet once again, with Gary leading Jimmy to the school roof where a fight begins. Jimmy beats Gary, with the pair falling through the glass roof and into Crabblesnitch's office. Crabblesnitch, who heard that Gary was the cause of everything, after being untied by Jimmy, expels Gary, who is then dragged out of the office by Jimmy. Despite being expelled, Miss Danvers continues to make announcements over the public announcement system calling him to Crabblesnitch's office and small talk claims that he is hiding in the bell tower of the Academy and living close to Blue Skies Industrial Park with the Townies.
Meeting Gary In Free Roam
- During the first mission Welcome to Bullworth, he can be seen standing next to the soda machine and then outside of Jimmy's Dorm room. He can be interacted with, but won't speak and will fight if provoked, and attacking him will not fail the mission, but knocking him out will.
- In the mission The Slingshot, if you jump out of the tree and run to where Gary is sitting, the mission will end and he will be walking around, and will fight if provoked.
- During the mission That Bitch, if Jimmy doesn't have any stink bombs in his inventory, he'll meet Gary outside the Girls' Dorm. Gary can be interacted with normally after the cutscene ends, and will fight if provoked but will usually run away if taunted.
- After the mission The Big Prank, Gary can be seen in the hallway in his Halloween costume. He can also be seen walking around anywhere else if the mission is failed, and will fight if provoked.
- During the mission Help Gary, he can be interacted with and will fight if provoked, but this will fail the mission.
- In Bully, Gary could be seen occasionally on campus or at Blue Skies Industrial Park. This glitch was fixed in later copies of the original game (Greatest Hits) and the enhanced Scholarship Edition.
- Gary appears in a deleted cutscene in Chapter 3, part of which can be seen on the "Holiday Special" trailer. He talks to Jimmy about how "young love... is a beautiful thing", and then pantomimes doggy style sex while saying "spank me". It is probable that this cutscene was removed due to sexual content, which could have hurt Bully's T rating. Not only was the cutscene removed from the game but the dialogue for it was removed from the data files entirely.
- There is a false but persistent rumour that Gary is a werewolf.
- In the mission Halloween, his physics are reverted from small to large, possible because of a coding error.