Randy Wagstaff, played by Maestro Harrell, is an enterprising eighth-grade student who is dependent on social services. He is a pupil at Edward Tilghman Middle School and is friends with Namond Brice, Michael Lee and Duquan "Dukie" Weems. He lives with a foster mother, Miss Anna, who seems to instill some discipline in his life. He is well known amongst his peers for his imagination and ideas. Randy runs a small business selling snacks and drinks to his peers and neighborhood drug dealers.
Although he shares the same last name as "Cheese" Wagstaff, it is unclear if he is related to the older Lieutenant. By following that family tree he would then be related to "Prop Joe" who although is often frustrated by his family, seems to take care of them throughout the series.
In a dispute with a rival gang of young pushers, Randy came up with the idea of filling water balloons with urine and ambushing the other gang. The plan backfired somewhat when Namond burst a balloon on himself but Randy escaped unscathed, while Michael and some of his unknown friends are brutally beaten. He also attempts to make money by catching homing pigeons to sell to drug kingpin Marlo Stanfield for his pigeon coop.
Randy was naively involved in the murder of local drug dealer Lex. Lex's colleague Lil Kevin paid Randy to give Lex a message that would lead him into a trap set by Stanfield soldier Chris Partlow and Snoop. Little Kevin later told Randy of Lex's fate and gave him more money. Randy was troubled by his involvement.
Randy receives money from Stanfield drug dealer Monk Metcalf as part of an effort by Marlo Stanfield to ingratiate himself to neighborhood kids. Randy loses the money to Western district officer Eddie Walker when he is chased away from a car stolen by his friend Donut. Walker refuses to believe Randy's story that the money is from his foster mother and pockets it, telling Randy his mother can come to the district headquarters to reclaim it.
When the school year begins Randy ingratiates himself to his home room teacher Roland Pryzbylewski with a hand shake and assists his teacher in controlling the class. When Prez is distracted, Randy asks permission for a hall pass and then takes several passes from Prez's desk. He uses the hall passes to get around the school selling candy and snacks to the other students during lunch periods. To blend in with the other grades Randy wears layers of clothing so that he can don the appropriate color uniform for the grade he is selling to.
Randy's scheme gets him into trouble when he is caught in the sixth grade cafeteria by Miss Reese, who recognizes him from her class two years ago. He is sent to Assistant Principal Marcia Donnelly's office. She threatens to tell his foster mother about his actions unless he gives her information about who has been graffitiing school property. Randy complies with her demands. He continues to cut class to sell snacks. He is enlisted by another student to act as a lookout while he has a sexual tryst with a female student in a bathroom. Randy is reluctant to get involved but does so anyway, earning five dollars for his efforts.
Lex's murder continues to trouble Randy. He discusses Chris Partlow's activities with his friends who tell him that Chris is a zombie master. Randy believes his friends and begins to fear that Chris will come after him. When Chris visits Michael on another issue Randy assumes he has come to ask about him. His friends tease him about his fears. Randy talks to Dukie about his worries and Dukie tells him that Chris is a murderer. He shows Randy a dead body Chris has hidden in a vacant building to convince him. Despite his promise to Dukie not to share the secret, Randy offers his knowledge of the murder to Mrs. Donnelly after she discovers his role in the bathroom incident; the girl involved claimed to have been raped.
Randy is suspended from school for acting as a lookout in the bathroom incident. Donnelly also puts him in touch with the police. Prez intervenes and approaches Cedric Daniels to protect Randy from the system. Daniels puts Randy in the care of Sergeant Ellis Carver. Carver interviews Randy to find out what he knows and then returns him to his foster mother, reassuring her that Randy is not a bad kid.
While suspended Randy accompanies Miss Anna to the polling station on election day. While he waits for her he picks up a days work delivering campaign material. He recruits Dukie, Donut and Little Kenard to help him. Donut steals a car so that they can travel around more easily despite Randy's hesitance. Randy loses his workers when they learn that he was paid up front and decide to take their share of the money wihtout completing the job. Randy carries on the work alone.
Carver turns Randy over to his old partner Thomas "Herc" Hauk because he is desperate for information about the Stanfield organization. Herc misjudges Randy and believes he is lying about not actually seeing Lex's murder. He pressurizes Randy to admit that he was there with little success. Herc believes that Randy is useless and allows him to return home.
Tiff eventually drops the rape allegation and Randy's suspension is lifted. He returns to school to find his math class transformed - Prez is teaching the class probability through dice and card games and a new computer has been set up. His friend Michael is suspicious of his time away from school and subtly warns Randy against getting involved as an informant for either the police or the teachers.
Word of the conversation between the police and Randy soon leaks out to the streets and Marlo's crew. The word is soon spread that Randy has been speaking to the police and he is labeled as a snitch in the streets. Randy is walking with Michael and Duquan when he is confronted at school by a group of students who want to fight him for being a snitch. Although Michael protects Randy and fights the kids off which leaves the leader of the kids bloodied and badly injured, Randy himself is beaten badly. Word soon gets back to Carver that Randy is in trouble around school and in his neighborhood and puts a police car on lookout at Randy's house promising Randy that he's going to take care of everything. People looking to hurt Randy notice the car and make a false police call from a nearby telephone booth to get them to leave the scene. With the cops gone, molotov cocktails are thrown into the house burning it down and putting Miss Anna in the hospital indefinitely and leaving Randy without a foster parent.
In the season finale, Carver tries his hardest to help Randy find another foster parent but to no avail. Randy ends up going back to a group home. There Randy still hasn't escaped his "snitch" title and ends up getting into fights with the other older hostile kids in the home.
Randy is briefly seen in the Season 5 episode "The Dickensian Aspect", where he is approached by Detective Bunk Moreland about Lex's death. Randy has noticeably "bulked up" and no longer wears his trademark smile on his face. Clearly affected by his time in the group home since the end of Season 4, Randy refuses to cooperate with Bunk and insults him in front of many of the other kids, and promptly tries to push a younger child down the stairs.
The scene shows how the system has chewed up Randy, just like Carver said it would. Once a young, innocent, happy child; Randy has became yet another casualty of a flawed system and seems desensitized to many things around him.
Randy is naive, as he becomes initially involved with the disappearance and murder of Lex; this causes him with trouble. Randy has a happy demeanor and somehow has a scheme of selling snacks to children younger than him.
Entertainment weekly named the character one of the five most interesting characters in season four.