It seems like a cliché now that bullies, while aggressive and cruel, are really sad, pathetic individuals with little to no self esteem. Jimbo Jones typifies this cliché, but since his character is never overused, it comes off as subtle and clever rather than hackneyed and corny. Jimbo is regarded as the leader of the bullies at Springfield elementary, since he usually takes the initiative over Nelson, Kearney and Dolph and does the talking.
But Jimbo is extremely self-conscious. For example, in “The Homer They Fall,” when Bart refuses to trade belts with Jimbo because his is an extension cord, prompting Kearney to say “Hey dude, he’s ragging on your cord,” Jimbo loses control and chases Bart. It is clear that Jimbo feels ashamed of his extension cord belt. In “Lisa’s Date with Density,” Lisa calls Jimbo a “crumb-bum” and Jimbo responds with “No one calls me a crumb-bum!” and he is visibly enraged. Jimbo feels his self-image is vital to his survival, and it takes little to crush his sense of self-esteem.
Not only that, but Jimbo resents talk of his mother for precisely the same reason. Later in “Lisa’s Date with Density,” Jimbo asks Kearney and Dolph “Why’s [Nelson] wasting his time with that Simpson chick?” From behind Nelson responds “Because your mom had a three-month waiting list.” While the other bullies triumphantly welcome Nelson back into their group, all Jimbo can do is look distraught and say “What’d he say about my mom?” Jimbo is hung up on what others think of him and his family. Jimbo’s “dishing it out” skills are paragon, while his “taking it” abilities are sorely lacking.
Jimbo’s aggressive behaviour is a result of his insecurity. In fact, his upbringing has little to do with it. In season six’s “The PTA Disbands!” we get a glimpse of Jimbo’s home life. When the teachers are on strike, Jimbo stays at home with his mother and watches soap operas. The living room is decorous, complete with a sculpted fireplace, marble bust, roses and heavily-cushioned couch. But it is Jimbo’s behaviour that is most surprising. Jimbo sits with his mother, sipping lemonade and eating finger sandwiches. He chokes up and says “I just can’t believe Stark would stoop to that — and right in the middle of Montana and Dakota’s wedding.”
What makes Jimbo sympathetic is that he feels he has to hide his true feelings. When we see him at home, we see the “real” Jimbo, unhindered by what others think of him.