Rob the Mob, directed by Raymond De Felitta and starring Michael Pitt and Nina Arianda, adapts the story of real life criminal couple Thomas and Rose Marie Uva, who dared to screw with the mob.

John Gotti was on trial. A rat was making sure Gotti would be convicted in order to save himself from seeing the inside of a jail cell, revealing mob secrets in the process. Little did anyone know, a recovering crack addict and a small time thief was using the courtroom as a classroom, taking notes about mobster social clubs and their rules – specifically the fact that no member was permitted to enter armed.

The opening credits of Rob the Mob set the scene for New York City in 1991. “Live Nude Girls” signs, pizza joints and graffiti make up the landscape and inflammatory headlines run across the city’s dailies. Tommy (Pitt) and Rosie (Arianda) are introduced while attempting to hold up a Queens flower shop on Valentine’s Day. He goes to jail; she gets a job at a collection agency that likes to hire convicts. After 18 months in jail, Tommy is released and joins her there – eventually taking up the social club heists as a lucrative side gig. It’s not long before Rosie’s fully committed to being the Bonnie to his Clyde.

Pitt is undeniably talented at playing the sensitive soul with a lawless streak. He delivers his character’s sometimes senseless sentences and most ill-conceived ideas with a passion and conviction that makes it easy to forgive Rosie for believing in him. He’s a poster boy for the charismatic conman, while Arianda conveys a mixture of naiveté and ambition as Rosie. Rosie wants to build a simple, honest life with Tommy, but becomes seduced by the money and the fame – as evidenced by her willingness to chat with reporter Jerry Cordozo, played by a subdued Ray Romano.

On the flipside of the story is the mob, with Andy Garcia as the don Big Al. Garcia inhabits the role of Big Al with an aristocratic air, which sees him eager to pass on a few life lessons to his fatherless grandson – including how to make the perfect arancini – before the authorities come to collect him from his home. There’s also the pressing matter of suppressing the duo making fools of the mafia and exposing the fact that they truly are organized.

Underlying the high-stakes stickups in which Tommy inexpertly wields an Uzi, and the pressure the authorities are placing on the mob, there’s a hefty dose of humor. In one stickup, Tommy forces a group of wiseguys to strip down to their unflattering underwear before they take to the streets to try to track him down. There’s also the smarmy manager of the collections agency that serves as the film’s major clown part.

Rob the Mob paints the story of Tommy and Rosie as both romantic and tragic. By the end, it’s hard not to feel sorry about their fate. Yet, at the same time, it’s difficult not to wonder how two people could be so rash and daft not to expect such an end as they received. As far as mob comedies with a heart go, De Felitta’s Rob the Mob is certainly such a spectacle to view.