Jimmy is an insecure child with a propensity to cry. He wishes to become famous, and is most often seen spending most of his time with Sarah. Jimmy is accident-prone (usually seen sporting many bandages and band-aids), and is the weakest child in the Cul-de-Sac (as evidenced in "Cry Ed," when his foot broke after a clothes-peg bounced onto it). Though Jimmy has a cowardly and delicate personality, he wishes to be strong and muscular. He can be crafty when motivated, and twice formulated scams that were very successful - even getting back at the Eds with one particularly cunning scheme. Jimmy has shown how deeply attached he is to Sarah when someone tries to take her away from him. Jimmy shows excellent cooking skills in some episodes, using his "Easy-Bake"-style oven to make soufflés and, on one occasion, cookies that were shaped like sailors.
Role in the series
Jimmy may seem weak and girly, and enjoy dolls more than monster trucks, but he has a darker side in addition to his more commonly seen infantile persona. When the show first started, Jimmy was very accident prone and was teased a lot, especially by Eddy and Kevin. He was nervous in most every situation, especially those which did not fit into his and Sarah's world of dolls and tea parties. Over time, however, he becomes a mischievous, sneaky little kid who frames the Eds and learns to scam people. There is still a lot of teasing going on in his life, though, and he is still in most cases a wimp.
In earlier episodes, Jimmy can usually be seen playing with Sarah, her telling him what to do and when to do it and watching over him like he is her son or, perhaps, a little brother. This setup seems to work well for them both. Jimmy is happy with his cooking, gardening, and dolls, as well as the bossing around from Sarah that comes with the territory. He puts up with Sarah's bossiness because anyone who wants to get at Jimmy must go through his redheaded bodyguard. In addition to protecting him in the physical sense, Sarah also protects Jimmy emotionally. When Rolf insults Jimmy’s quiche in "Pop Goes the Ed" by stating that it is a cursed food and has in turn cursed the party, Sarah comforts the crying Jimmy and says that she like to eat quiche, which seems to be all that matters to Jimmy.
Again in the Season 2 finale "Cry Ed," it's Sarah who is constantly on hand to put the accident-prone Jimmy back together, while drawing the other kids' sympathy away from attention-seeking Eddy. He does show that he has an angry side on occasion, though. In Season 1's "An Ed Too Many," he takes out his frustration at Sarah's apparent infidelity first on a teddy bear, then on Jonny, and finally on a gloating Eddy. Although these attempts at releasing his rage are futile (except when practiced on the bear), they do show that Sarah to some extent acts as a buffer, keeping him from being violent. In Season 3's "Wish You Were Ed," Sarah pushes him into a rage by constantly complaining about his driving skills, and this shows that even she is not immune to his anger. As the show progresses, it seems that Jimmy is much tougher than he would appear after a cursory glance.
Season 2 seems to be the real turning point for him. This is perhaps a direct result of being turned into Eddy's reluctant protege in "Ed in a Halfshell." This is disputable, however, as the harder edge revealed more explicitly in later seasons starts developing even before Season 2's 22nd episode. He begins to display a sharper attitude, a sharper tongue, and reveals himself to be a natural when it comes to fleecing the masses, turning into a ruthless money-hungry businessman with a success rate that Eddy can only dream about. From this point on, though he is still most comfortable being passive, Jimmy continually proves that he can hold his own when he has to. In fact, he displays a rare and somewhat unnerving talent for behind-the-scenes work–in "If It Smells Like an Ed" he sets the Eds up three times: once at the start, framing them for ruining Friendship Day; once near the end, where he makes the kids believe the Eds committed crimes against Jonny; and as a finale, he has the Eds dragged off by the Kankers. He does all this simply because Eddy humiliated him in front of the other kids by giving him a wedgie. It is apparent after viewing this episode that he's quite dangerous.
Jimmy doesn't really know what to make of the Eds and their scheming. He wants to trust them, and most of all, see good in them. You'd think Jimmy would learn his lesson after falling for each successive scam, but he never does. Worse, if Eddy caters to and strokes Jimmy's ego, it causes him to be tricked even more easily. This is Jimmy's greatest weakness, and Eddy's biggest advantage over him. Blinded by his quest for respect, fame and glory, in love with the concept of being loved, he's prepared to go to any length, even if it means ditching Sarah and her good advice. One episode that proves this is Season 4's "One Size Fits Ed," where Jimmy allows Eddy to force-feed him megatons of peaches and cream under the premise of becoming famous. He also leaves Sarah with very few qualms in "Hands Across Ed."
Jimmy is interested in fashion and art. Anything to do with the arts, be it painting, directing, or performing in front of an audience leaves him positively alight with anticipation. Jimmy's highly evident artistic talent allows him further scope to gain attention (often, like Eddy, to the point of milking it.) He revels in his own extreme delicacy, for he believes nobody suffers like an artist. This has mixed results, naturally. It's a wonderful thing that your artistic soul, burdened by the misery of trials such as waxy build up on fruit, and your cookies getting burned, means you're never short of sympathy from your friends. This can lead to being spurned when they get sick of hearing about this, however, although this does not often happen.
Jimmy is also very accident-prone. While he is certainly most noted for his fluffy hairdo and that distinctive retainer, he's also likely to be seen sporting a myriad assortment of Band-aids, bandages, and plaster casts. Delicate and fragile to the extreme, it seems there's always something wrong with Jimmy, be it a bandaged nose, a splinted arm, or a simple bump on the head. He gets seasick, rubber tires give him a rash, hopscotch makes him dizzy, he doesn't like being alone, doesn't like strange foods, gets freaked out by camera flashes, bad breath makes him faint, scary stories frighten the jujubes out of him, and Eddy makes him very nervous. Whenever he's not ailed physically, it seems that something's wrong either mentally or emotionally.
Jimmy gets on well with all the cul-de-sac kids, although he's wary of loud-mouth Kevin as he often makes fun of him for being a weakling. He knows nobody's really going to get him, because he has a fiercely loyal bodyguard who will spring to his defense at the first whimper. He does join in with group games and Urban Rangers activities, but he's happiest (and safest) when he's with Sarah. Sarah may tell him what to do, but she doesn't tell him what to be, and so he's free to talk about tea sets, curtains, the latest fashions, or offer to style Sarah's hair without fear of rebuke or mockery.