Craig "Bolo" Chirumbolo, is a typical stoner. He plays the drums in a band called Merlin's Monocle, along with his friends Kevin and Lawrence, who he calls Murph and Lex. In his first appearance he hangs out with the two of them, smoking marijuana under a bridge and discussing simplistic hypotheticals. He has an attraction to former first lady, Jackie Kennedy, because she's "so sad."
He reads the presidential trivia off the labels of Whitehouse Beer and seems to have them memorized, a skill he used to help Kevin pass his history homework.
Like Kevin, he enjoys the band Shire of Frodo, and believes in preserving the purity of rock and roll.
Bolo has a tendency to lie, or brag about himself. Mainly, when it comes to sex. Despite obviously being a virgin, he claims he has had sex many times. He tells obvious lies, such as the claim that after sex, you get really cold, or that his summer girlfriend died of leukemia and polio. He also claimed to be street-wise, and knowledgable about where and how to buy cocaine, but in reality he was only basing his ideas off of what he had seen on TV.
Because of his neglectful parents, Bolo is often able to take his mother's car to drive his friends around, despite being only 14 (Kevin also takes the steering wheel from time to time).
The three friends enjoy petty vandalism, as seen when they egg cars on Halloween. Bolo's name can also be seen graffiti'd on the bowling ally bathroom stall that Bill uses.
Bolo and Lex are not loyal friends to Kevin, as they abandon him when he goes back for his dad's record and he specifically asked them to wait. They also make fun of Kevin for having a panic attack, and Bolo refused to listen to Kevin's reasons for being apprehensive about playing their gig at Vic's. Despite this, however, the two of them are supportive of Kevin in many ways and give him confidence in areas Kevin's dad does not.
- He has a pet turtle.
- His mother doesn't know how old he is.
- He is hinted to be bisexual.
- Bolo is usually the one to provide marijuana, or other drugs, for his friends.