James 'Jimmy' Two-Shoes is a perpetually optimistic, thrill-seeking 14-year-old boy. It is shown to be almost impossible to get him upset and he is rather ignorant of the faults in others. He has a mission to spread happiness to Miseryville which makes him a source of irritation to Lucius Heinous whom Jimmy nicknames "Lucy". He owns a pet monster named Cerbee, whose demeanor is very similar to that of a dog.
He is often seen doing extreme activities despite Heloise's warnings. Jimmy is also oblivious that Heloise has a crush on him, due to the fact that whenever she tries to do something nice, it always backfires and turns to an evil plan. Jimmy and Heloise are the only two humans regularly featured in Miseryville. Jimmy's or Heloise's parents have never been seen or mentioned. Heloise's aunt who appeared to be human did visit in one episode though.
Jimmy is an optimistic, outgoing, and enthusiastic boy who is always friendly towards everyone he meets. He is best friends with Beezy and Heloise and is happy and courageous enough to help others in danger. Jimmy is naïve and gullible and usually ignores any of Heloise's warnings but will usually need to go to her if something goes wrong. Jimmy can sometimes get competitive and greedy with others to get something he wants.
He has a super hero identity named Power Squid where he wears a squid on his head, a mask and purple gloves.
Jimmy is usually a nice guy but he has lost his temper if annoyed e.g in "Dance Jimmy Dance" he was mad at Beezy and Heloise for going to a dance contest without him and telling him that he couldn't dance.
In "High School Mule-sical" when the mule was making fun of him he kicked it across the stage.
And in "Jimmy New-Shoes" when he tried to get his old shoes back but was told they had been sold he got upset and yelled.
Also In Good Old Jimmy Jimmy has gotten furious of everyone telling him he was to young to do things that was only allowed for grow ups, that lead him to screaming into a mailbox.
In the episodes Too Many Jimmy's and Head Will Roll, Jimmy stated that volleyball is his favorite sport next to soccer.
It's strongly implied that Jimmy is not native to Miseryville and hasn't lived in Miseryville for very long, as shown in a few episodes, e.g. he doesn't know about hibernation in 'I Am Jimmy' or didn't know the definition of "grounded" in Miseryville (literally means being buried to the head up in sand and/or dirt). He also was unaware of spring break he was also aware of concepts like snow carnivals and chocolate that where unknown to most mivilans pryor to his revilling them. Though where he comes from or how he came to Miseryville is never thought on.
Jimmy is generally clueless of Heloise's crush on him. In "There's Always a Hiccup!", he was reluctant to kiss her. He also rejected the opportunity to kiss her in "I Am Jimmy".
However, he has shown some affection to her on several occasions. He was worried about her losing her job in "Catalogue of Misery". He complemented on her dress in "Scent of a Heinous". He was the only one who wanted to rescue her in "Henious vs Clown" and he was trying to get her attention in "Misery Hearts" by offering to finish her romance novel for her after she gave him a cold shoulder and only payed attention to Beezy.
In "Heloise Schmeloise" Jimmy falls in love for first time with a robot clone of Heloise named Schmeloise. Jimmy becomes Schmeloise's boyfriend and makes Heloise insanely jealous. Schmeloise ends up being destroyed at the end of the episode, which breaks Jimmy's heart.
The second time that Jimmy's ever had a crush was in "She Loves Me" when he and Beezy find a girl in a tower named Princess Arianna. Both try to impress her, not knowing that she is actually a monster.
In the episode "Heloise's Secret Admirer" Heloise dates Peep (Jaymee Two Squirrels) after being given a gift and flattering note. When Jimmy found out she had a secret admirer it gets suspicious but when he found out its Peep, Jimmy gets jelious of her new boyfriend and believe that their relationship is been forgotten and Heloise rejects Peep as his boy friend and chose Jimmy as her new boyfriend.
In Better Sweater Jimmy fell in love with Heloise because of the sweater (showing his affectionate side), he mentions that 'he could not hide his feelings for her', so he has feelings for Heloise but is unaware of it.
- Beezy (Best friend)
- Cerbee (pet)
- Heloise (girlfriend )
- Saffi (Beezy's ex/girlfriend)'
- Lucius Heinous VII (Beezy's dad)
- Jez (Lucius' girlfriend)
- Peep (son of Rudolpho, in love with Heloise)
- General Molotov
- Jimmy one shoe