Harold "Hi-Top" Jones was the son of Angeltop and an unnamed African-American jazz singer (whom she had killed). He lived with an aunt, his father's sister. He was also the grandson of the infamous Flattop.
Hi-Top's name was derived from his "hi-top fade" hairstyle. He shared some of the physical characteristics of his family, specifically heavy eyelids, freckles, and pronounced lips. Hi-Top had a habit of speaking in rhyme (and thought balloons also revealed that his thoughts were in this format as well).
Association with Little Boy
When he first ran afoul of Dick Tracy, Hi-Top was an inner-city teenager who was affiliated with a street gang called the Crypts. Hi-Top killed Tim Vick (another teenager) for his sneakers. This brought inner-city violent crime to Dick Tracy's attention.
Hi-Top received an invitation from Little Boy (who claimed to be the grandson of Big Boy) to join his new criminal empire. When Hi-Top arrived at the meeting place, he was assaulted by Mousse, a henchman of Little Boy. Hi-Top subdued his large assailant, which impressed Little Boy.
Little Boy's goal was the unite the various rival gangs into one organization, and he believed that Hi-Top was essential to that plan. Hi-Top had recently transferred to a suburban high school and he helped recruit another student into Little Boy's organization: Restless Mahoney, the niece of Breathless Mahoney.
Hi-Top was arrested by Tracy after being questioned about dealing drugs. Tracy noticed Vick's initials on the bottoms of Hi-Top's sneakers and held him on suspicion of murder. Hi-Top was released bail soon after, which was paid by a lawyer provided by Little Boy.
Around this time, Hi-Top began to dress in a more sophisticated style, eschewing jeans, sneakers, and windbreakers in favor of a suit and tie.
Tracy and the Major Crimes Squad raided Little Boy's hideout. Tracy was captured and Hi-Top and Little Boy planned to kill him, but Restless turned on the two young men. She held a gun on them and demanded that they free Tracy. Hi-Top fled the scene but was arrested. Having just turned 18, he was now old enough to be jailed and tried as an adult.
Hi-Top was mentioned by Sam Catchem during the investigation of a possible affiliation between Blowtop Jones (Hi-Top's great-uncle) and Stiletta Jones (Hi-Top's grandmother). Tracy commented how few of the surviving members of the Jones family had a good relationship with the police, but he did not specify if Hi-Top was still in prison.
- Hi-Top's hairstyle was inspired by that of Christopher "Kid" Reid of the popular hip-hop group Kid 'N Play.
- The storyline and relationship dynamic of Little Boy/Hi-Top/Restless was crafted to mimic the relationship that those characters had in the 1990 Dick Tracy feature film that had debuted in theaters that year.
- While Hi-Top expressed a dislike for police in general and Dick Tracy in particular, he does not seem to be motivated by a desire to avenge his family members. He therefore does not meet the criteria of a "Revenge-Seeking Relative".
- The fact that Hi-Top's last name was "Jones" (his mother's name) may indicate that his parents were never married, but this has not been confirmed.