Hold onto your hats! Originally entitled "The Shiny New Enemies," Chain of Fools begins with a newscast telling us that this rare Ming Dynasty coin set of three was stolen. We hear this in Kresk’s room as he wakes for work. He gets dressed, writes a note (a suicide note, as we learn) and heads for the bridge. There we see him observe a body floating in the water. He dives in and we get the first of several flashbacks. To follow this story, crafted like a Stephen King novel with nested flashbacks, you need to note that "at the bridge"—plot-wise, is the top level of the story.

We flashback to Kresk’s barbershop where Avnet arrives for a haircut. Kresk is a bit of a loser and Karen, his wife, who is running off with the marriage councilor, interrupts the haircut. She wants him to dog-sit for her at her apartment. Kresk overhears Avnet on his cell phone talking about how he stole the Shiny New Enemies. When Avnet tries to kill Kresk, the gangster slips on shaving cream and falls into a pair of scissors, which lodge in his neck. To get rid of Avnet’s body, Kresk enlists the aid of an overgrown boy-scout, Andy, who helps him carry the body to what is supposed to be a deserted spot, but turns out to be crowded with joggers. They finally opt to hide the body at Karen’s house. (Remember the dog-sitting)?

Kresk tells Andy about the Shiny New Enemies and they decide to get them from Avnet’s apartment (they have his key). There, Avnet’s boyfriend, the drag queen, Miss Cocoa, surprises them. After an altercation, Miss Cocoa is knocked out by a piggybank, which contains the Shiny New Enemies. Kresk takes the coins and flees just as Mikey, the teen-age hit man shows up. He misses them and Avnet and calls his client, Bollingsworth, on his cell phone. We flash to Bollingsworth, who wonders how he ever got involved in this mess anyway.

In a deeper level flashback, we are taken to the crime scene, where Bollingsworth, who is a stuffy British entrepreneur, has joined the gangster Avnet to "heist away." In a deeper flashback, we learn that Bollingsworth hates the president of the museum, Melander Stevens and will do anything to embarrass him. Melander brags that the Shiny New Enemies are arriving and gives Bollingsworth the full details (stupid man). Another flashback shows Bollingsworth hiring Avnet at a penny arcade. "I’ve heard you’re one of the craziest motherfuckers around," he says in his British butleresque accent. He also tells Avnet that the most disreputable coin collectors are in France, where the Shiny New Enemies can be fenced.

Back to the heist, Bollingsworth and Avnet share a Pastrami on Rye sandwich, then rob the armored car. When Avnet threatens to shoot Bollingsworth, he escapes by throwing the sandwich at him. At the business club the next day, while Bollingsworth gloats over Melander’s loss, Detective Kolko (famous for her Policewoman centerfold in Playboy) arrives to investigate the crime. She has one piece of evidence—a Pastrami on Rye sandwich with two bites in it, "just like the one you’re eating there," she tells Bollingsworth. He gets a call on his cell. It’s Avnet (in the Barbershop—we’ve been there) threatening to blackmail him.

Bollingsworth decides to hire a hitman to rub Avnet out. Through a local mobster, Paulie, he gets connected to Mikey (Elijah Wood), a seventeen year old hitman, who despite his age is as cold as steel. His principal credential is his hit on Senator Dove (as we can see for ourselves in another Flashback, where Mikey enters the senator’s hotel suite, beats him up and rolls him off the balcony). Bollingsworth wants the hit to happen that afternoon. "Well, it’s your lucky day. I’m not busy this afternoon."

Mikey goes to Avnet’s and misses Kresk and Andy by a few minutes. The story continues with Kresk leaving Avnet’s body at his wife’s place. Back at his own apartment, his sister Jeannie arrives. She was dumped by her boyfriend and needs to leave her son, Scottie with Kresk for a few hours. Scottie is the kid from hell and hates his uncle. While Kresk is trying to find a place to pawn the Shiny New Enemies, Scottie swallows them. They rush him to the hospital, where the x-rays show the coins will pass in a few days. Jeannie arrives, takes her son and calls Kresk a loser.

At this point, the story returns to Top Level and we are at the bridge, where Kresk is ready to jump. He says, "Goodbye cruel world," but notices Bollingsworth on another part of the bridge also committing suicide. "Goodbye cruel world," says Bollingsworth, hurling himself into the drink. Kresk dives in and saves him. Bollingsworth goes into a coma and is hospitalized.

Detective Kolko interrogates Kresk at the hospital. He’s attracted to her. He is coached by Bollingsworth’s personal assistant, Mr. Kerner, to recant his report on the suicide. "He fell in." After finding out that the most disreputable coin collectors are in France, Kresk decides to take his nephew to France to poop out the coins. He and Andy abduct Scottie from the schoolyard.

Kresk visits Bollingsworth in the hospital. When Bollingsworth briefly awakes from his coma and accuses Kresk of stealing the Shiny New Enemies, he decides he needs Bollingsworth rubbed out. He goes to his old High School nemesis, Paulie (the mobster) who fronts him the money for the hit—with Mikey. When he meets Mikey, he doubts such a young man can do the job. Mikey tells him "I don’t like to brag, but do you remember Senator Dove." We are then treated to another flashback of Senator Dove’s demise at the hands of the brutal teen-age hitman. Mikey changes his attitude a little when he finds out that Kresk’s father committed suicide. Mikey’s parents, dentists, also committed suicide. In the funniest single moment in this movie of funny moments, Mikey bursts into tears and is consoled by Kresk. Perhaps, he shouldn’t take the hit, suggests Kresk. "I’ll make the hit," Mikey cries in a high pitch baby’s voice. (Iconic moment).

Paulie decides he made a mistake floating the up front money for the hit and is now going to muscle Kresk. After Kresk and Kolko hook up for a dinner interrogation, he learns that her father committed suicide. Paulie and his henchman go to Kresk’s to rub him out; only they meet Andy (tied up by Scotty) and Scotty (a menace to any bad guy). Andy and Scotty tell Paulie (stupid them) about the Shiny New Enemies and that Scotty has swallowed them. They knock Andy out and abduct Scotty.

At the hospital, Mikey enters Bollingsworth’s room to do the hit. He admits to the comatose Bollingsworth that (Flashback: Senator Dove committed suicide. Mikey was just the room service lad who interrupted him). Just as Mikey’s ready to pull the trigger, another hitman arrives (hired by Kerner) and Mikey agrees to let this second hitman do the hit. However, when this hitman turns the gun on Mikey and asks him if he has any last words, Mikey says (predictably), "Goodbye cruel world." Miss Cocoa (who is a nurse at the Hospital) interrupts them. Mikey flings a bedpan at the other hitman and, in the ensuing shoot out, escapes.

Kresk and Kolko, now hot under the collar, arrive at Kresk’s and get passionate. Before they go to bed, Kresk’s wife interrupts having arrived home and found something unexpected in her apartment. Kresk thinks its Avnet, but in a, you guessed it, flashback, we see Avnet waking up, going out to the balcony and falling off. Karen berates Kresk for nearly killing her dog.

Kresk and Kolko head for bed. When she asks for protection, Kresk goes into the bathroom for some, where he finds, stoically sitting atop the toilet—Mikey, who reports in. While Kresk tries to get rid of him, Mikey admits he wants a friend and asks Kresk out for some coffee and a show. Kresk sternly rejects Mikey’s friendship. The hitman departs, pissed off, through the bathroom skylight.

Meanwhile, Kolko has found a gun and the tickets to France. She intends to arrest Kresk now and take him as her collar. Andy (who has been in the other room) conks her with the door. She’s unconscious. Kresk and Andy go off to save Scotty. In the shooting gallery rescue, Andy gets winged and Paulie and the Henchman shoot each other. They get Scotty (who is now full of prune juice), and rush off to the hospital to attend to Andy’s wound.

At the hospital, Mikey arrives to complete his hit. "A job’s, a job." He’s interrupted again by the second hitman. The Hamletian Mikey yields and asks the hitman to kill him, as life's not worth living. As the two hitmen have a Sartrian discussion about life, Bollingsworth wakes, sees the two guns and dies of heart failure "Oh, Bollocks!" Mikey asks the hitman to a show; and they go off together to see Cats.

Andy has a flesh wound. Scotty goes off to poop. Kolko arrives at the hospital and finally Kresk levels with her, telling her about Avnet and the scissors in his neck. She doesn’t believe him until Avnet is wheeled in with the sartorial weapon stuck in his jugular. The case is solved and Kresk and Kolko are in love. But Scotty poops in a hospital toilet, which automatically flushes the Shiny New Enemies down the sewer. The coins go out to sea and are swallowed by a big fish. The credits roll over Kresk, Scotty, Kolko and Andy fishing off a pier, reeling in the fish, but letting it escape into the river as the fish that got away (with the Shiny New Enemies). Amen.