Charles Caldwell School Uniform

  "In a few years the world will be filled with shit music ruling the airwaves." -

Charles Caldwell

Charles Daniel Caldwell is the protagonist of Charles' Time at Bullworth. He is currently a junior, like his best friend Michael Diaz.


Charles stands at 5'11 and weighs 155 lbs. He's skinny & a decent fighter, who can move somewhat fast. He has medium length dark brown hair and blue eyes. He usually doesn't wear the uniform, until he is threatened with expulsion to wear it. Towards the end of his juinor year he grows out his hair & facial hair, but eventually goes back to his normal style.


Charles is nice to people, however, if someone was to get on his bad side, he isn't above being a jerk to them. He wouldn't want them to come to harm, but he doesn't want to be friendly to them either. He is known to overreact to small things, such as someone sitting on his car hood, comments from other people, etc. He will always go out of his way for his friends. Charles is insecure about himself, which makes his luck with women not very good. He doesn't like the popular kids, as he thinks they get handed everything for doing nothing. He also thinks lowly of himself, such as feeling his friends would be better off without them, but will not mention it when around them. Charles is also paranoid of the government, and distrusts it.


Charles Caldwell Casual Outfit


Charles was born in Cincinnati, Ohio and remained there until he went to Bullworth Academy for his Sophomore year. He has some family he still keeps in touch with, but he doesn't mention them. He also has a history of criminals within his family, which everybody looks down on him for. He once went to a concert and was thrown out for starting a massive fight because a drunk guy punched him in the face. After getting tired of Cincinnati, he hopped a plane to Bullworth and has been there for a year.


Charles has numerous fears, those of which include:

  • Alcatraz Federal Penitentary
  • The Paranormal
  • Heights
  • Airplanes
  • Chernobyl


Michael Diaz(best friend): Michael saved Charles from the jocks and the two have been friends since that very day. Michael now lives with Charles in his dorm room after he got into a fight with his stepfather. Michael usually pokes jokes at Charles' luck with women, among other things, but Charles always fires back with a clever remark. The two can usually be seen either making fun of the jocks, or just watching tv.

C-Money(best friend): Charles met C-Money the day he met Michael, and the two have been friends since the day Charles helped C-Money out with the G.S. Crew. Charles usually turns to C-Money for serious things, since both guys have been through a lot in their lives. Charles parks his car right next to C-Money's car. Charles & C-Money start to sorta-have a falling out during C-Money's senior year.

Greg Ryder(best friend): Greg and Charles first met at the pier and Greg beat the living hell out of Charles, proving that Charles is sorta-weaker than Greg. Since the day after he apologized for going bat-shit on Greg, the two have become friends. Both share the same interest in music, tv, movies, etc. Both are also pot smokers, and often smoke together when by themselves. According to Greg the two of them are "As thick as thieves".

Nicole & Bradi: At first Bradi thought Charles was a psycho because of how he acted in public. After hanging out with Charles, they became friends and Bradi didn't think that Charles was a psycho anymore. Nicole hasn't really been featured that much in Charles' story yet, but will be.

Gary Smith: Ever since the day Charles helped C-Money ruin a drug deal between the G.S. Crew & someone else Gary(the leader of the G.S. Crew) has made it his personal mission to kill Charles. Charles hates Gary as much as Gary hates him. Johnson had Gary re-enrolled at Bullworth to finish his seinor year.

Whitney Fordman: Like Michael, Charles is also enemies with Whitney. Charles has almost beat him in fights, but Whitney usually has his size advantage over Charles. So far, Michael is the only person to defeat Whitney. After Gary returned to the academy it isn't known what happened with Whitney.

The Jocks: Charles is bitter enemies with The Jocks, and has been since day one. He has a personal grudge against Ted, Damon, and Casey. The Jocks have made Charles living hell, but he's beaten them easily.

The Preps: The only prep Charles is on good terms with is Parker, but the rest of the Preps hate him. Although, after Parker & Bradi break up again, Parker blames Charles and now he hates him.

The Bullies: Charles is on neutral terms with the Bullies.

The Greasers: Charles was enemies with them for a while, but eventually after burying the hatchet with ex-leader Johnny Vincent, he told the Greasers to ease up on Charles.

The Townies: Charles really doesn't consider them a clique at the school, so he's on good terms with them.

The Prefects: Charles hates the prefects, and has even beaten up a few of them.

Dr. Crabblesnitch: Charles sorta-likes Crabblesnitch, but ever since he didn't do anything to stop Charles' humiliation at the basketball game, he's held a personal grudge against him.

Assistant Principal Johnson: Charles considers the assistant principal his #1 enemy when dealing with the faculty. He holds a grudge against Charles, Michael, Greg, & C-Money, and favors The Jocks. He is the reason Greg left Bullworth (but he later returned), and got Gary re-enrolled. When drugs later appear on campus, Charles and his friends are blamed and threatened with expulsion, but Charles lets Johnson expel him instead, so he can take the fall for everyone else.

Jimmy Queen: Jimmy is a new friend to Charles. Jimmy is usually the victim of bullying, but his friends always stick up for him.

Patrick Davidson: Patrick is a new student at Bullworth, who stands at 6'5, has curly dark brown hair, and is very strong. He challenged Charles to a fight on his first day but was knocked out by Charles after one hit with Patrick's own brass knuckles (although he basically pummeled Charles before). Patrick has helped Charles out with a lot, and Charles considers him a close friend.

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