|“||'Cause it's fun. It's fun to do bad things.||„|
|~ Lamilton Taeshawn|
Lamilton Taeshawn is a juvenile delinquent child and he is more malicious than other villains in The Boondocks series. Lamilton appears in "Smokin With Cigarettes" as the episode's main antagonist.
He enjoys doing bad and unhealthy things regardless of the consequences, he even says so himself. He abuses his grandmother and other people. He does not care for anyone not even himself which makes make probably suicidal. And he appears to be emotionless and without a conscience.
He was taken into therapy by Dr. Doomis when he was 5 because of his sociopathic tendencies and 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.
Much later he was released despite the insistence that he be locked up, upon his release he steals his grandmother's car and invites Riley to join him which he does and offers him a cigarette which he is addicted to. He goes on a rampage and nearly hits many people before he eventually runs out of gas where he is interviewed by the press and he has no regrets. Later his grandmother forces him to apologize to the Freeman's for endangering Riley where she explains his background and how his parents and cousins were abusive to him and each other, which Granddad finds the story boring so he forces them to leave.
The next day he is caught assaulting his grandmother at a Wali-Mart because she told him he couldn't have any fried chicken and he is interviewed again, with 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 pass and causing them to crash, spraying them with a mixture of urine and hot-sauce, and upturning a port-a-potty with a man inside.After that he invites him over to his house to watch horror movies. Riley finds them to be too violent and disgusting and asks why he likes them, he responds that he likes seeing people get hurt and die, and Riley begins to feel uncomfortable around him so he decides to leave, before he does, he shows him his grandmother's handgun and Riley tells him to put it away. Later that night he tells Riley to help him rob an old lady's house so he can get more guns and her attack dog jumps out at them and Riley tries to tell him to leave before they get caught but he shoots the dog killing it which he claims was in self-defense despite it being tied up.
Dr. Doomis who had been following them calls the cops for Lamilton's killing of the dog but he gets released later that day, afterwards he begins to stalk Riley and waits outside until his class is over and he confronts him about supposedly snitching on him and tells him that he will kill him for it, and Riley convinces him that it was wrong and that he will be friends again, and once Lamilton has his back turned Riley tackles him and takes the gun from him and runs up to the school's rooftop where he follows him and Riley throws the gun off the roof so he won't use it again, and Riley asks him what he is going to do now and in response. Lamilton attacks him and starts to beat him up and attempts to strangle him to death. Uncle Ruckus stops by to investigate but since they are black he doesn't care and tells them to proceed killing each other, using this distraction Riley fights back and gains the upper hand eventually knocking Lamilton off the roof. Riley grabs a hold of his hand and Lamilton pretends to apologize for everything he did and tells him to pull him back up. Riley tells him he's too fat, Huey, Granddad, and Dr. Doomis arrive at the scene and Doomis makes Riley let go of Lamilton's hand and drops Lamilton apparently causing him to fall to his death. Riley feels bad for him and Doomis tells him he deserved to die at that moment Granddad points out that he's gone, but then notices him limping away and Doomis is horrified that he survived and jumps off the top of the roof fighting and grabbing Lamilton saying he will have to destroy him, which Lamilton tries to avoid Doomis, it is unknown what happened to him after that.
- Lamilton is based on the real-life young delinquent named Latarian Milton, the 7 year old who jacked his grandmother's car and went for a joyride, quotes such as "I like to do bad things" and "my friend who smokes wit cigawettes" are said by both Lamilton and Latarian. He is therefore one of the most evil characters in the boondocks.
- Dr. Doomis and Lamilton's relationship is a reference to both Dr. Loomis and Michael Myers in the Halloween franchise.
- Lamilton is very similar to Henry Evans. Both are juvenile delinquents who befriend the protagonist, both are completely insane and cruel and do evil things for fun, and both kill a dog. Also, both end up falling from a high place (a (School) building for Lamilton, a cliff for Henry), though Lamilton survived due he fat safe his fall, while Henry is presumed decreased due he not to be found at sea leaving him officially dead.