James “Jimbo” Jones, Sr., also known as Jamesbo, Dr. J, and Hector Gutierrez, is one of the bullies at Springfield Elementary, with Dolph Starbeam, Kearney Zzyzwicz, Nelson Muntz, and the Weasels. He is a 6th grader.
Jimbo is the second-in-command of the bullies, being the leader when Nelson isn't around, although Nelson has no interest in hierarchic systems. Jimbo is the tallest bully, and strongest after Nelson. He constantly bullies other smaller children at Springfield Elementary and, like Nelson, has an on-and-off friendship with Bart Simpson.
Jimbo wears a purple knit cap (originally no knit cap), a black short-sleeved T-shirt, emblazoned with a menacing skull (originally, a yellow short-sleeved dress shirt), blue jeans, and black and white shoes. Bart describes him as a good looking rebel who plays by his own rules.
A real low-life, Jimbo is acknowledged as the leader of the bully gang in absence of Nelson. Jimbo is often seen hanging out with Dolph, Kearney, sometimes Nelson, and occasionally Bart. He is considered an outlaw or a "good boy". Despite his reputation as a bully, it is sometimes hinted that Jimbo is in fact Christian, with strong moral standards. At one point, when he reveals to Martin that the "paint" vendor that he got the unicorn tattoo from was actually a tattoo parlor at the Skewed Over event, he notably showed hesitance at beating up Martin at that point as he "had it rough already", even stating to the other bullies that it might not be a good idea to beat him up, although he ultimately decides to beat him up with the other bullies. He has been kicked out of all 4 Space Mutant movies. According to the episode "Beware My Cheating Bart", he has a bald spot underneath his hat (although he didn't have it earlier in Bart of Darkness or Lisa the Drama Queen).
Jimbo's parents are Mr. Jones and Carol Jones. It is often implied that his mother is sexually promiscuous, possibly working as a prostitute. It is also stated that Jimbo's mother and Kearney have been sexually involved sometime in the past. She sometimes walks around topless, which impresses Kearney and Dolph. Jimbo has a sister; he, Nelson, Kearney, and Dolph use the case from her retainer as an ingredient in a pumpkin pie for Bart at Thanksgiving.
He is one of the best looking boys in town along with Dolph. Jimbo also use to have a skateboard, just like Bart. He smokes cigarettes and drinks alcohol with Dolph. Jimbo also uses marijuana and other drugs. It is also implied that Jimbo has a job as a police informant. Lisa saves Bart from the bullies, Jimbo says to Bart, "It's a lucky coincidence, you happen to be your sister's brother.". Another time, Jimbo laughs at Bart's pajamas, and mockingly asks if his mommy bought them for him. When Bart replies, "Of course, she did. Who else would have?", Jimbo looks blank for a while before saying that Bart has won (this time).
Jimbo enjoys intimidating his classmates and shoplifting (even with Kearney). His best friends are Dolph and Kearney, and he is also close friends with Nelson. Jimbo also has a decent friendship with younger yet more popular fellow troublemaker Bart Simpson, despite the fact that Bart himself is not a bully and, from time to time, is also subjected to the abuse of Jimbo and the other school bullies. It is hinted that he comes from a well-off family, displayed when (with the school closed for a teacher's strike) he and his mother watch soap operas and sip tea together in a very nice living room. Given that Jimbo's father, Mr. Jones, seemed to be a beer-drinking lowlife when seen in another episode, it may be that Jimbo is an illegitimate child. His mother may be involved with "bad boys". He was kidnapped by Stewie Griffin in "The Simpsons Guy".
Jimbo is the second-in-command of the gang of bullies at Springfield Elementary School consisting of him, Kearney Zzyzwicz, Dolph Starbeam, Nelson Muntz, and the Weasels. Jimbo constantly bullies other children and has on many occasions been shown to beat up Nelson, even though he is friends with him.
Jimbo temporarily became the boyfriend of Bart's 15-year-old babysitter and next door neighbor Laura Powers, whom Bart had a crush on. However, he got even one night when Laura was babysitting him and had Jimbo over. Bart made one of his trademark prank calls to Moe's Tavern and told Moe when he found out that it was a prank that his name was Jimbo Jones of 1094 Evergreen Terrace (Note that the Simpsons' address was inconsistent in the early seasons). Moe came to the house with a rusty knife and Jimbo started to cry and arrested by police officers pathetically. Laura broke up with Jimbo shortly afterwards.
Jimbo temporarily became Bart's friends like Milhouse and next door neighbor Bart Simpson, whom Bart warns Jimbo to paying Homer, Marge, Lisa, and Maggie a visit at 742 Evergreen Terrace. However, he got even staying with Bart when Jimbo was come visit to Bart's bedroom and had Homer over. Marge made on of his trademark homeschool for Jimbo and Bart to go on Olde Springfield Towne and told them when they found out at it was a Fort Sensible that has Sandy Petersen. But Jimbo warns Bart to stop the army general of Fort Sensible, and hop on general's horse and made one of their trademark prank calls to army general and told him "(it's time for you to cut the Indians in.) Actually, we will cut your horse-twerp out." And finally they wanted to spend for the rest of the year to stay here with Homer, Marge and Lisa, on Season 4, 5, Season 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, and all of the seasons of the years.
Jimbo suggests that he stole Lisa's Malibu Stacy dolls because, "they demean women." At one time, Homer told Jimbo, "Your king commands it." Jimbo boldly replies, "Jesus is our only king." In "Mypods and Boomsticks," it's stated by Bart that Jimbo is Christian.
Non canon appearances
An issue of the Simpsons Comics revealed the backstory of Jimbo. When Jimbo was a new student at Springfield Elementary School, he wore a yellow short-sleeved dress shirt, a pink tie, and blue jeans; in those days, there were nerdy bullies, so nerds ran the school with a mix of high attendance, GPAs and cruelty. Jimbo's shirt gets ripped off by nerdy bullies when the nerds pushed him on a chair with glue on it. Willie gave Jimbo the T-shirt that he now wears, and he was nicknamed "Jimbo" because of his low IQ. A water balloon snapped the hairband that held his hair in a ponytail, and Willie gave Jimbo the purple knit hat, that we now associate with him. Now, Jimbo looked like a bully, but he hadn't become a bully yet, then Bart told Jimbo that he should beat up the nerds.
Note: this however contradicts the flashback in the episode, Lisa's Sax, where Jimbo was first introduced as the official school bully, by Principal Skinner.
According to Simpsons Comics 57, he is allergic to bee stings.
Treehouse of Horror
He was killed and was made into burgers in Treehouse of Horror V.
Behind the Laughter
Jimbo is loosely based on the character John Bender from The Breakfast Club. Jimbo is named for the Executive Producer, James L. Brooks. He is voiced by Pamela Hayden (Tress MacNeille in The Telltale Head).
In The Simpsons comics, Jimbo comes to school as "James Jones." Although James is referred to as "Jimbo," that is not actually his real name. Although Nelson once referred to Jimbo as "James," Bart realized that Jimbo's real name is "Corky" in Season 7's "Bart the Fink" (though in Season 8's "Lisa's Date with Density," Nelson refers to Jimbo as "James" when he is defending Lisa, implying that "Corky" could be a nickname or a pseudonym). This may or may not be true, but in the end, it says that Jimbo's real name is "James." Jimbo's other known aliases are Jamesbo, Dr. J and Hector Guterriez.