Three Italian Heist Films You Need to See
Welcome to an incredibly enjoyable trilogy of crime comedies starring Marcello Mastroianni and Vittorio Gassman
Ciao ragazzi! Benvenuti! I love Italian cinema, especially from the 1950s and 60s. I’ve been treating myself to the lighthearted crime films of Dino Risi (more on that soon), lately, but I’ve been meaning to rewatch a delightful trifecta of Italian crime comedies starring the beloved star Vittorio Gassman, Italy’s “Il Mattatore” (so-called after a Risi film that he leads). Now that Halloween is over, and we can return to our normal crime programing, I thought we should kick things off Italian-style. Check these out. The first one is genuinely one of the best capers ever made, and the sequels are a lot of fun.
Allora… divertitevi!
Big Deal on Madonna Street (1958)
Mario Monicelli directs a crack cast in this wonderful Italian caper which stole my heart. Spoofing Rififi a little bit, it’s a perfect gem of a comedy—Vittorio Gassman plays Giuseppe “Peppe il Pantera” Baiocchi, a petty crook with dreams of being a big-time thief, who plans a perfect pawnshop heist on a quiet block in Rome. But once word gets out about his plot, all manner of unscrupulous characters come out of the woodwork and hope to take part in it. It’s an ensemble cast like you’ve never seen before (hello Marcello!), a phenomenal farce, and an all around fantastico time.
Fiasco in Milan (1959)
This sequel to Big Deal on Madonna Street sets our favorite band of thieves (still led by Il Mattatore!) after a big-time heist. This time, they have to steal a suitcase of money (containing the pool of bets over soccer tournaments). As you might expect with these guys, though, things don’t go according to plan. Unfortunately, the sequel is not as good as the first, but hey, Claudia Cardinale is in this one!
Big Deal After Twenty Years (1985)
This sequel to Fiasco in Milan doesn’t live up to the second and definitely doesn’t live up the first, although it does at least attempt to do something new, rather than repeat the success of the first film. In this third chapter, directed by Amanzio Todini, Tiberio (Marcello Mastroianni) is now the main character, fresh out of prison and reuiniting with his old friends from the gang, Peppe (our hero from the last two movies) and Ferribotte.
Olivia Rutigliano
Olivia Rutigliano is an Editor at Lit Hub and CrimeReads. Her other work appears in Vanity Fair, Vulture, Lapham's Quarterly, AirMail, the Los Angeles Review of Books, Public Books, The Baffler, Bright Wall/Dark Room, Politics/Letters, The Toast, Truly Adventurous, and elsewhere. She has a PhD from the departments of English/comparative literature and theatre at Columbia University, where she was the Marion E. Ponsford fellow. She hosts the podcasst "Culture Schlock" at Lit Hub Radio. She is on instagram at @oldebean, twitter at @oldrutigliano, and bluesky at @oliviarutigliano.bsky.social.
