The film begins with two small-time criminals, Tommy Uva and Rosie DeToma, who, high on drugs, decide to rob a florist on Valentine's Day. While Tommy brandishes a gun at the cashier, Rosie waits anxiously in her father's car. Unfortunately for Tommy, he is apprehended and sentenced to 18 months in prison. In the interim, Rosie secures a position at a debt collection agency helmed by Dave Lovell, a former inmate himself, who had previously swindled a whopping $800,000 from major corporations using fraudulent invoices. Now reformed, Lovell is keen on giving Tommy employment upon his release, hoping for a chance at redemption. However, Tommy’s restless nature leads him to deviate from the prescribed call scripts, often giving clients dubious advice on how to cheat Lovell’s business.
As Tommy finds himself seething with anger upon spotting local mafia members in his neighborhood — whom he views as "fat old guys living off their reputation" — the backstory of his family emerges. His father had taken a mafia loan to start their shop and suffered brutal beatings for being late with payments, a trauma that ultimately impacted Tommy deeply. While his mother and brother continue the family business, his mother attributes the heartbreak leading to his father’s death to Tommy’s descent into crime. Conversely, Tommy harbors a belief that his father's demise is entirely due to the mafia's relentless humiliation.
In a pivotal moment, Tommy skips work to witness John Gotti's trial, where he gets a surge of excitement as he hears Sammy the Bull testify about the no-gun policy in mafia social clubs. With this information, Tommy devises a bold plan to rob a club that Sammy mentioned, believing it would be a low-risk venture since no one would be armed. He procures an Uzi, albeit with no prior experience in handling such a firearm, and with some reluctance, Rosie assists him in getting it ready.
During their audacious heist, Tommy recklessly fires the Uzi into the air to intimidate the mafia members into surrendering their valuables while also indulging in humiliating antics, like messing with their hair. As he departs, he defiantly shouts, “This is for Frankie Uva.” While Tommy and Rosie are elated with their successful heist, the mafia is left raging. Sal consults with his superior, Big Al Fiorello, who prefers scaring the duo rather than eliminating them due to the increased scrutiny on organized crime because of Gotti's trial.
The pair's luck doesn't last long as they soon run out of funds and embark on another robbery, this time stripping mobsters down to their underwear for further humiliation. Unbeknownst to them, FBI agents are surveilling the club and photograph the bewildered mobsters after the chaotic getaway. Agent Frank Hurd shares the scandalous details with columnist Jerry Cardozo, who, with some reluctance, features the story prominently, further deepening the mob's embarrassment.
Encouraged by their new notoriety, Tommy and Rosie convince Lovell to join their escapade at the trial. They hang on every word of Sammy’s testimony, which leads them to an opportunity at another club. However, upon robbing the Waikiki club, they encounter only a handful of elderly men, including Joey D, who pleads for the return of his wallet — a keepsake from his deceased wife. The wallet holds a treasure trove of information: a complete list of the mafia’s inner workings, with names, ranks, phone numbers, and addresses.
Understanding the gravity of their find, Tommy and Rosie decide to inform the mafia about the list, seeing it as a form of insurance against their retaliation. Rosie even ventures to call Big Al to issue a warning. Meanwhile, the mafia is left fuming, especially as they realize the importance of the list and decide to put out a contract on the infamous duo, now dubbed "Bonnie and Clyde."
As tensions mount, Rosie reaches out to Cardozo to express her dissatisfaction with the media’s portrayal of their robberies. Their presence in the headlines draws dangerous attention, prompting Lovell to caution them about the perilous path they’ve chosen. The situation escalates when a mafia underling spots Tommy and Rosie and quickly informs others of their whereabouts, sealing their fate.
The FBI manages to infiltrate their apartment, reproducing the critical list that ultimately leads to Big Al’s arrest. Shockingly, Cardozo learns that despite their crucial role in the investigation, no protection will be afforded to Tommy and Rosie. Desperate, he even offers them tickets to Mexico, but they insist they have a plan. They take a final trip to Manhattan to relish the sights of the holiday season.
In a heartbreaking turn, their adventures come to a tragic end when they are ambushed in their car. The film closes with the poignant image of Tommy and Rosie alongside a note that declares the list they pilfered led to several significant mob convictions.
