06/19/2010 05:12 am ET | Updated Jun 26, 2013

The Heist Picture

Welcome to the topsy-turvy world of the heist film, where most often the authorities are the dupes, and the crooks, daring heroes.

How do heist movies make this work? First, since usually the bad guys are in effect the protagonists, we get to know them as living, breathing characters. They gradually tap into our innate sympathy for the underdog, outcast, and rebel. The heist itself may come to represent the bigger challenges in our own lives, since the same elements determine success: instinct, intelligence, daring, meticulous preparation, teamwork, and leave us not forget - sheer luck.

These films generate considerable dramatic (sometimes, comedic) tension, since high-stakes thieves are the ultimate gamblers: no amount of skill can fully eliminate the core risks involved, or the role of arbitrary fate.

Sounds like fun, no? For my own short-list of outstanding heist pictures, read on.

First, one of the quintessential film noirs is also a heist film: John Huston's The Asphalt Jungle (1950). A realistic, detailed chronicle of the planning, execution, and aftermath of a daring jewel robbery, Jungle is first and foremost a superb mood and character piece. Huston coaxes compelling performances from the entire cast, including Sam Jaffe, a young Sterling Hayden, and in particular, Louis Calhern as the smooth but quietly desperate mastermind. (Also look for an early Marilyn Monroe appearance as Calhern's stunning, almost child-like mistress.)

Hayden would go on to work with a younger but equally talented director, Stanley Kubrick, on The Killing (1955), a documentary-like depiction of a race-track robbery. This early entry from the Kubrick canon delivers skillfully paced, edge-of-your-seat entertainment, featuring vivid characterizations. In particular, Elisha Cook, Jr. and Marie Windsor stand out as a wildly dysfunctional couple. Spare yet potent, The Killing lets you witness the budding of a cinematic genius.

Two excellent heist pictures were made by the very same man, the gifted Jules Dassin, who in the early '50s, under the cloud of the Hollywood Blacklist, left a successful directing career state-side to work in Europe. His first feature, made in France, was Rififi (1954), about a group of jewel thieves as distrustful of each other as the police - and not without reason. Viewed today, the movie retains its gritty realism: the justly famous heist sequence, done completely in silence, is riveting, and Jean Servais's performance as the crime's originator conveys a sad, twisted nobility. The conclusion of this small masterpiece will grip you and remain with you long after the closing credits.

Ten years later, Dassin released Topkapi, starring his wife, Greek actress Melina Mercouri, Maximilian Schell, and Peter Ustinov. This scenic, colorful movie (shot largely on location) constitutes lighter comic fare, with a motley crew of crooks attempting to steal a jewel-encrusted dagger from the heavily guarded Topkapi museum in Istanbul. Breezy and clever, the well-cast stars clearly are enjoying themselves, except perhaps for sad-sack Ustinov (no matter - he won Best the Supporting Actor Oscar for his performance anyhow).

In addition to Topkapi, my three heist comedy picks would have to be two Alec Guinness comedy classics made with Britain's fabled Ealing Studios: The Lavender Hill Mob (1951) and The Ladykillers (1955), along with a third, lesser-known Italian chestnut, Big Deal On Madonna Street (1958).

Mob is the story of a seemingly timid but sly clerk who plots the perfect robbery of his own bank. This intricate crime's planning and execution precipitate some of the more inspired comic sequences you'll see on film. Among the film's slew of Britain's finest character actors, the ever-charming Stanley Holloway, best-remembered as Alfie Doolittle in 1964's My Fair Lady, plays off Guinness beautifully. Movie buffs: also look fast in the first scene for a momentary glimpse of a future star, Audrey Hepburn. (Her bit character's name is "Chiquita"!)

Directed by Alexander Mackendrick, The Ladykillers actually refers to a rag-tag bunch of lower-rung thieves and hoods, led by the smarmy Professor Marcus (Guinness). To provide convenient, suitable cover for their upcoming caper, they all board at the home of a frail, elderly widow, one Mrs. Wilberforce (Katie Johnson), posing as musicians. Unfortunately for them, Mrs. Wilberforce is a good deal smarter and more alert than she appears, and the gang find themselves spending more time fending her off than planning the robbery. Guinness is priceless in a hilariously ghoulish turn, and Miss Johnson nearly steals the picture as the diminutive but strong-willed landlady. Both Peter Sellers and Herbert Lom (who'd reunite in the Pink Panther series), both appear as members of Marcus's motley gang.

Finally, Mario Monicelli's Big Deal, starring Vittorio Gassman, Marcello Mastroianni and Claudia Cardinale, unfolds in the broader, more expansive Italian style, with lots of yelling and frantic gesturing throughout. This particular assemblage of would-be crooks, attempting to reach a safe located in the local pawn-shop, may rank as the most bumbling in history, defying all logic or reason. Monicelli's manic romp is crowd-pleasing in every way, thanks to hilarious performances from Gassman, Mastroianni, and the rest of the ebullient cast. The director focuses as much on his sad-sack characters as he does on the details of the heist, and it's impossible not to find these inept robbers completely endearing. Delightfully over-the-top, Big Deal is great fun for those who prefer their comedies with a hearty dose of Italian passion.

Moving back to dramatic territory, Dog Day Afternoon (1975), a personal favorite, reunited director Sidney Lumet and Al Pacino, who'd worked previously on Serpico. This fact-based, Oscar-nominated drama tracks two scheming misfits (Pacino and the late John Cazale) who've attempted to rob a New York City bank during a heat wave, and very quickly imprisoned themselves in a no-win situation. Pacino's ruffled, passionate evocation of working-class Brooklynite Sonny - who riles the gawking crowd outside the bank with chants of "Attica!" - stands alongside his best work of the 1970s. Cazale, who played weak brother Fredo in The Godfather, is heartbreaking as Pacino's imbecilic partner-in-crime. Gritty, suspenseful, and superbly crafted, Afternoon is a bona-fide Lumet classic, always worth revisiting.

Next we fast forward to Reservoir Dogs (1992). Quentin Tarantino's darkly funny, extremely bloody directorial debut was brought to life through the efforts of star Harvey Keitel, who was impressed with the unconventional script. Jumping back and forth between the aftermath of a botched robbery and the meticulous, pre-heist preparations of ringleader Joe Cabot ('50s B movie star Lawrence Tierney), we follow the intertwined fates of a motley group of hired rogues who address each other with color-based pseudonyms to protect their anonymity. Mr. White (Keitel) races to a rendezvous spot with howling gunshot victim Mr. Orange (Tim Roth), only to be met by Mr. Pink (Steve Buscemi), who's convinced someone in their group has tipped off the police. Things only grow more complicated-and disturbing-when the others arrive.

For still more recent fare, try Michael Mann's Heat (1995), a pulsating thriller detailing the cat-and mouse maneuvers between an implacable detective (Al Pacino) and seasoned criminal (Robert de Niro), who leads both an armored truck robbery and a bank heist. Here is a contemporary heist film that pulls out all the stops. Electric, graphic and brutal, Heat is not for the squeamish, but if you think you can take it, strap yourself in and hold on. It's an intense, riveting ride, with DeNiro and Pacino backed up by the likes of Val Kilmer, Jon Voight, Tom Sizemore, and Ashley Judd. Also look fast for a young Natalie Portman playing Pacino's mentally fragile step-daughter.

These great heist movies work by tying us to the unfortunate characters who populate them, and investing us in the outcome of their attempts to reach the same pot of gold so many of us chase, however flawed or doomed those attempts may be.

And of course, in doing all that, they also give us that most satisfying of sensations: the vicarious thrill.

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