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'Cause it's fun. It's fun to do bad things.
~ Lamilton Taeshawn's famous quote.
Everybody says I'm crazy, but I don't care. I don't care about my grandmother, I don't care about that dog, and I don't even care about myself! And since we ain't cool no more, I don't even care about you!
~ Lamilton threatening Riley Freeman, making it very clear that he doesn't care about anyone, not even himself.

Lamilton Taeshawn is the main antagonist of the episode "Smokin' with Cigarettes" in The Boondocks. He is a juvenile delinquent with a very destructive and malicious personality.

He was voiced by Bobb'e J. Thompson.


Lamilton enjoys doing bad, unhealthy, and insalubrious things regardless of the consequences; he even says so himself. He is excessively vituperative, insulting, and abusive towards his grandmother and other people. He does not care for anyone, not even himself, which makes him probably suicidal (Not likley as feared falling off the school roof to his death), nihilistic, and destructive. He also appears to be emotionless and unconscionable.


He was taken into therapy by Dr. Doomis when he was five because of his sociopathic tendencies, but 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. As a result of this mindset, Lamilton's grandmother filed a restraining order against him.

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 Freeman to join him, which he does, and Lamilton offers him a cigarette, which Lamilton 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 has no regrets. Later, his grandmother forces him to apologize to the Freemans for endangering Riley and 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.

The next day, Lamilton is caught assaulting his grandmother at a Wali-Mart shopping store because she told him he could never 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.

Lamilton with a handgun blackmailing and threatening Riley.

After that, Lamilton invites Riley over to his house to watch horror movies. Riley finds them to be too violent and disgusting and asks why he likes them, to which 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, Lamilton 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. 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 to confront 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 with him again, and once Lamilton has his back turned Riley tackles him, takes the gun from him, and runs up to the school's rooftop, where Lamilton follows him and Riley throws the gun off the roof so he will never use it again, and asks him what he is going to do now. 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 does not 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, and Huey, Granddad, and Dr. Doomis arrive at the scene.

However, Doomis dashes past the Freeman family and makes Riley let go of Lamilton's hand and drops Lamilton, apparently causing him to fall to his death. Riley is horrified and feels bad for him while Doomis tells him Lamilton deserved to die. At that moment, Granddad points out that he's gone, but then notices Lamilton alive and limping away. 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, while Lamilton tries to avoid Doomis. Lamilton begs for someone to notify his grandmother because Doomis is violating the restraining order. It is unknown what happened to him after that. Either Doomis killed him and ended his madness or someone answered his request to call his grandmother and she saved him in time.


  • 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.
  • Dr. Doomis and Lamilton's relationship is a reference to both Dr. Loomis and Michael Myers in the Halloween franchise.
  • Lamilton has been regarded as one of the most evil (if not the most evil) Boondocks villains, probably even more evil than Colonel H. Stinkmeaner.
  • Lamilton is the only person in the series that Riley was able to beat in a one on one fight, without interruption.
  • His grandmother claimed that he came from an abusive family hinting that childhood abuse is what made him become who he is.
  • Despite appearing in only one episode, Lamilton arguably had lasting effects on season 3, as his actions caused Riley to become less villainous and psychotic after seeing how evil Lamilton was.

External Links



Freeman Family
Huey Freeman | Riley Freeman

Ruckus Family
Uncle Ruckus | Bunny Ruckus | Mister Ruckus | Nelly Ruckus

Wuncler Family
Ed Wuncler I | Ed Wuncler II | Ed Wuncler III

Colonel H. Stinkmeaner | Rufus Crabmiser | George Pissedofferson | Esmeralda Gripenasty

Gin Rummy | Lamilton Taeshawn | Luna | Kardashia Kardashian | Boss Willona | Deborah Leevil | Siri | The Booty Warrior | Butch Magnus | Slickback | The Devil | Colonel H. Stinkmeaner (Clone)