Lamilton Taeshawn is a 6 and later 8 year-old Afro-American juvenile delinquent. He is very malicious and says that he enjoys doing bad and unhealthy things. He abuses his grandmother and other people. He does not care for anyone, not even himself. He is even believed to be the 'anti-Christ'. Lamilton was voiced by Bobb'e J. Thompson.
Lamilton is a sociopath, who does whatever he wants (i.e stealing, driving his grandmother's car, smoking, etc), without any regard for the law. He has a macabre sense of delight in horror movies, where the death scenes are too violent and graphic, saying he loves to watch people get hurt/killed.
He's shown a degree of nihilism, as he had stated to Riley that whatever happens to others (including himself) is of no concern to him, and that doing "bad things" was the only thing that mattered, feeling absolutely no remorse for his actions.
However when he nearly fell off the school roof, he apologizes about everything he had done. Although since he was only in one episode, it's unknown if he changed his ways.
He made his first (and only) appearance was in "Smokin With Cigarettes". He was taken into therapy by Dr. Doomis when he was 6 because of his sociopathic tendencies, although his behavior did not improve. Doomis described him as having black lifeless eyes like a doll's, and even said he might be the anti-Christ.
Two years later, he was released despite the insistence that he be locked up. At some point after his release, he befriends Riley, then steals his grandmother's car and invites Riley to join him. Riley accepts and Lamilton offers him a cigarette, which he is addicted to. He goes on a rampage and nearly hits many people before he eventually crashes in the parking lot of a Walli-Mart (a parody of Wal-Mart), where he is interviewed by the press and has no regrets. The next day, his grandmother forces him to apologize to the Freemans for endangering Riley, where she explains his background and how his parents and cousins were abusive to him and each other. Granddad finds the story boring so he forces them to leave, afterwards strictly forbidding Riley from seeing Lamilton.
Two weeks later, he is caught assaulting his grandmother at Walli-Mart because she refused to buy him fried chicken and he is interviewed once again, having no regrets. He later invites Riley to pull a bunch of pranks on the townspeople, including causing car pileups by throwing things from a highway overpass, spraying bystanders with a mixture of urine and hot sauce in a drive-by shooting, and upturning a port-a-potty with a construction worker inside.
At the end of the day, he invites Riley over to his house to watch horror movies that are very graphic. Riley finds them disgusting and asks why he likes them, to which he responds that he likes seeing people get hurt and die, and Riley, feeling uncomfortable, decides to leave. Before he does, Lamilton shows him his grandmother's gun and shows it off, much to Riley's shock. Later, Lamilton forces Riley to help him rob Betty Von Heusen's house so he can get more guns, only for her attack dog to jump out at them. Riley tries to tell him to leave before they get caught, but Lamilton shoots the dog dead which he claims was in self defense despite it being tied up.
Dr. Doomis, who had been following them, calls the cops for Lamilton killing the dog, but he gets released later that day. He then begins to stalk Riley and waits outside until his class is over. Lamilton confronts him about supposedly snitching on him and tells him that he will kill him for it, but Riley convinces him that it was wrong and that he will gladly be friends again. Once Lamilton has his back turned and walks away, Riley tackles him, takes the gun, and runs up to the school's rooftop where Lamilton follows him. Riley throws the gun off the roof and asks him what he is going to do now. In response, Lamilton attacks him. At first, he has the upper hand, beating up Riley and attempting to strangle him to death. Uncle Ruckus briefly intervenes, but since they are black, he doesn't care and tells them to proceed killing each other. Using this distraction, Riley fights back, eventually knocking Lamilton off the roof. Riley grabs a hold of his hand and Lamilton then apologizes for everything he did and tells him to pull him back up. Riley tries to and struggles and he tells him he's too fat and overweight. Huey, Granddad, and Dr. Doomis arrive at the scene and Doomis makes Riley drop Lamilton, apparently causing him to fall to his death. Riley feels bad for it and Doomis tells him "he deserved to die". At that moment, Granddad points out that his body is gone, but then notices him limping away and Doomis is horrified that he survived and leaps off the school roof and on top of Lamilton-he survives this too and tries to fight Doomis off threatening to call the police. It is unknown what happened to him after, as he is never seen or heard again.
- Lamilton is based on the real-life young delinquent named "Latarian Milton", the 7 year old who stole his grandmother's SUV and went for a joyride, quotes such as "I like to do bad things" and "my friend who smokes wit cigawettes" are spoken by both Lamilton and Latarian.
- Latarian Milton was also featured on an episode of the Comedy Central show Tosh.0 in a segment called web redemption, in which he got to explain the day he stole his Grandmother's SUV.
- Lamilton's character is a reference to the movie character "Michael Myers" from the Halloween series due to having a "pure evil" personality and his doctor casually named "Doomis" (which is also a reference to Michael's doctor: "Loomis") talking about Lamilton having "black lifeless eyes" while Loomis says that Michael has "the blackest eyes, the devil's eyes. And him limping away after supposedly dying.
- Lamilton was lying about having total disregard for the law and himself, as shown after Riley catches from falling off the roof, he begs Riley to save him and reveals that he has problems with his anger and that he doesn't want to die, and when Dr. Doomis attacks him he begs someone to call his grandmother and reminds him of their 100 yard restraining order.
- His grandmother claims that Lamilton isn't really a bad child as his attitude was caused by witnessing domestic abuse between his parents and other relatives at a young age, his mother drinking heavily and his father losing his job. She claims that there was a lot of tension in his home.
- Lamilton is so far the only person, who was defeated by Riley in combat.
- The second time Lamilton gets arrested, his mug shot shows him holding a mug shot board with the number "0666" on it. This could reference to him being so evil he is able to be compared to the devil, because the devil's signature number is "666".