The plot revolves around a group of small-time thieves attempting to burgle a pawn shop in Rome,[2] resulting in a series of comedic mishaps.

The main characters, portrayed by Vittorio Gassman, Renato Salvatori, Carlo Pisacane, Tiberio Murgia, and Marcello Mastroianni, collectively navigate the pitfalls of their ill-fated heist.

The film contributed significantly to the careers of Gassman and Mastroianni, with the former breaking into comedic roles previously considered unsuitable for him.

Claudia Cardinale makes a minor appearance in the film, playing a chaste Sicilian girl constrained by her overbearing brother, portrayed by Murgia.

Initially doubtful about the film's potential success, the producers strategically featured the comedian Totò on the original poster to generate audience intrigue.

He harangues his girlfriend and lawyer to get him released so he can carry out a heist idea stolen from another inmate, a dishonest bricklayer who purposely constructed a flimsy wall between a pawn shop safe and an adjacent vacant apartment.

Peppe takes up the heist plan with Cosimo's gang: Mario, a petty thief and the youngest member of the group; Michele, a posturing Sicilian crook who needs money for his sheltered sister's dowry; Tiberio, a down and out photographer caring for his baby while his wife is in jail on a minor offense; and Capannelle, an elderly pickpocket.

Tiberio steals a movie camera from a flea market and attempts to film the pawn shop safe's combination with a telephoto lens, but without success.

The rest of the group pressures him to accept so they can stage the burglary, but Nicoletta unexpectedly quits her job in a huff, and does not know if the spinsters will make their weekly departure.

Tiberio deposits his baby with his wife in prison to participate in the robbery, but runs into the flea market proprietor, who breaks his arm for stealing the movie camera.

After a couple of misfortunes, they succeed in breaking through a wall that leads to the apartment's kitchen; the elderly women had rearranged the furniture, thus disorienting the gang.

"[4] The apartment and pawnshop on "Via della Madonna" was in reality located at 7–8, Via delle Tre Cannelle (41°53′48″N 12°29′10″E / 41.896613°N 12.486°E / 41.896613; 12.486), immediately north of Trajan's Market.

[6] According to The New York Times, for its American release the film was "dubbed into English over a six-month period with considerable money and effort expended in matching voices and intonations to achieve artistic and mechanical perfection."

At the time, there was a general debate over dubbing versus subtitling foreign films, and the American distributor, Richard Davis, screened the first reel of both versions for critics and writers and asked for their preference.

"[8] Chicago Tribune critic James Rich liked the film, though he noted "the humor [is] tarnished only when the parade of subtitles makes viewing a sort of exercise in speed reading.

"[12] The Baltimore Sun said: "Director Mario Monicelli has endowed the film with such flashes of brilliance, and the cast...has enacted it with such tasteful understatement, that The Big Deal on Madonna Street must be listed as one of the funniest comedies of the last ten years.

"[14] The film was a hit in Italy when it was released and won two Italian Nastro d'Argento awards: Best Leading Actor (Gassman) and Best Screenplay.

[16] A sequel directed by Nanni Loy titled Audace colpo dei soliti ignoti (also known as Fiasco in Milan or Hold-up à la Milanaise) followed in 1959, reuniting the entire main cast, aside from Totò and Mastroianni.

Set in 1930s Chicago with an African-American cast and using popular songs of the era, the show opened at the Broadway Theatre on April 10, 1986, and closed on June 8, 1986, after 69 performances.