Will Carlson is a twenty-something loser who lives in a rundown neighborhood, where he ekes out a living as a birthday party clown in order to pay the rent for his abusive mother's nursing home and the mortgage on his rundown house. Despite the difficulties of the job, clowning is Will's one escape from the realities of his miserable existence: Will genuinely likes kids, and takes great joy from making them happy on their birthdays.
Struggling to make ends meet, but not wanting to give up his dream job, Will comes up with the idea to be a "bachelor party clown." Will's idea is that men throwing bachelor parties can hire him as well as a stripper; Will will enter the room prior to the "real" entertainment, wearing clown makeup and lingerie, tricking the bachelor into thinking that there was a mix-up and a gay stripper has been sent in lieu of a female one. After a few moments, the real stripper will enter, and everyone will have a laugh. Will invents the persona of Vulgar the Clown (after his friend tells him that the entire idea is "vulgar") and solicits himself in the want-ads. Before long, he is hired to appear at a bachelor party being held at a nearby seedy motel.
When Will arrives for the party-- wearing a teddy, garters, clown makeup, and a trench-coat-- he is attacked and brutally beaten by a middle ages man ,Ed, and his sons Gino and Frankie. The three men then proceed to gang rape Will, taking turns videotaping the attack. The trio hold Will hostage in the motel room for an indeterminate amount of time, during which they subject him to a series of violent and humiliating sexual assaults. Once it's over, the men let Will go, telling him that if he goes to the police and tells them what happened, the authorities will question the attack, as Will believed he was attending a bachelor party while dressed in women's lingerie. A tearful Will goes home and spends the remainder of the night and part of the next morning crying while he washes himself clean in the bathtub. It is implied that he contemplates suicide, as he slices himself with a piece of the mirror he himself breaks in a fit of rage.
Will spends a considerable amount of time after the attack in a crippling depression, which nearly costs him his home. Eventually, Will fulfills a promise to appear as a clown at one of his past-clients' children's party. When he gets to the party, Will discovers a hostage crisis is occurring; the father of one of the children, in the middle of divorce proceedings has kidnapped his own daughter and his threatening to kill her. Perhaps driven to heroism because of the rape, Will sneaks past the police barricade, breaks into the house, and subdues the father. News reporters capture some of the event on film, and before long the story makes national headlines. Will becomes known as "the hero clown;" the attention and outpouring of support breaks him out of his depression, and he is eventually given his own syndicated children's television show.
The media coverage attracts the attention of Ed and his sons (who are still actively torturing other young men). They threaten Will with a copy of the tape of his being raped and begin to extort him. When Will tries to pay the men off, they attack him in a bathroom stall. Will finally strikes an agreement with the men wherein he will come to a motel room and "perform" for them, allowing himself to be taken advantage of again, and they will give him all of the copies of the tape; secretly, Will plans to ambush and murder them with the help of one of his friends. When the time comes, Will finds himself unable to take a human life. Just as the men are about to rape and murder Will, they all become entangled with another lowlife at the motel; a shootout ensues, during which the man and one of Ed's sons are fatally shot. Ed's other son picks up one of the dead men's guns and, playing with it, accidentally shoots himself in the face. Ed panics, and Will chases him through the motel parking lot to a nearby playground. The combination of fear and physical exertion causes Ed to become short of breath; as Will approaches him, Ed drops dead of a massive heart attack. His conscience clear, Will retrieves the tape of his rape and goes on to live happily ever after, hosting his television show.
The director's cut DVD features an extended ending, wherein Will finds a note from Syd along with a clipped newspaper article on the Fanelli's death, Ed's heart failure from panic and overdose of crack cocaine, as well as attributing Ed's sons' deaths' to a random incidence of criminal violence. A stunned Will determines that the men's deaths were all karma for their evil.
- After the success of such films as Clerks, Chasing Amy, and Dogma, Kevin Smith financed three films (Drawing Flies, A Better Place, and this one).
- The film was written and directed by Smith's long time friend Bryan Johnson. Vulgar the Clown was also the View Askew Productions logo at one time.
- The lead rapist, Ed Fanelli, was inspired by Dennis Hopper in Blue Velvet.
- The Fanelli sons, Frankie and Gino, were inspired by the rapists of Deliverance.
- The movie was written in 28 days, filmed in 26.
- The role of Will Carlson was written specifically for Brian O'Halloran.
- Brian O' Halloran actually had to have a real bottle broken over his head in one scene because the budget was so small, that View Askew couldn't afford a break-away bottle.
- O' Halloran really cut his own hand on a piece of broken glass in one scene of the movie.
- Many of the grips, assistants, and film crew took bit parts in the movie (due to the incredibly tight budget).
- The film was sound edited and mixed at Skywalker Sound.
- Howard Stern got a copy of the film before it was released. His producer, Gary "Baba Booey" Dell'Abate is a big fan of Kevin Smith, so Scott Mosier sent a copy to him. After Gary saw (some of) it, he gave it to Howard, because he heard a clown is raped in it, he was expecting a silly campy comedy. When he got to it and he saw how serious it was, he was disgusted and repulsed by what he saw. He turned it off in revulsion and threw the tape in the garbage. He ranted on about it on the radio and had Kevin Smith on the show to ask him what he was thinking. He let out a particularly scathing review about it, but this just inspired people (including his own radio cast) to see the movie.
- Kevin Smith personally requested the role of Martan Ingram for himself.
- It was Bryan Johnson's decision to put a mismatched toupee on Jerry Lewkowitz.
- The film world premiered at the 2000 Toronto International Film Festival.