With intricate plots, multiple twists and turns, and gritty characters who live on the edge, heist movies have long been a Hollywood staple. Sometimes the thieves suffer the consequences of their actions and sometimes they get away with their crimes, but their carefully hatched plans almost always go awry. Here are nine of the best heist movies from Classic Hollywood.
One of the first crime films to show criminals in a more sympathetic light, director John Huston’s heist-gone-wrong starred Sterling Hayden as tough guy Dix Handley, a career criminal who meticulously plots an elaborate jewel heist, only to see his plans go awry in its aftermath. The tense and gritty look at the criminal underworld featured a stunning 11-minute sequence detailing the intricate job eventually leads to a series of disastrous double-crosses. Filmed in stark black-and-white with a documentary feel, The Asphalt Jungle heavily influenced a number of later crime movies, most notably Jules Dassin’s classic Rififi (1955) and Quentin Tarantino's Reservoir Dogs (1992).
After two low-budget indies, Stanley Kubrick made his first studio film with The Killing, a tautly-paced thriller about a veteran criminal (Sterling Hayden) planning one last heist before settling down to marriage. The heist in question turns out to be a $2 million score from racetrack, which he robs with a crew of small-timers, including a crooked cop, a betting window teller and a sharpshooter. Though they initially get away with the money, the crew suddenly finds themselves in way over their heads, as their well-executed plan falls apart after the betting teller makes the mistake of telling his duplicitous wife about the job. Initially panned by critics and a failure at the box office, The Killing – which demonstrated the young Kubrick’s deft ability at handling non-linear narratives – grew to be a film noir classic.
Not to be confused with Steven Soderbergh’s lighthearted romp from 2001, the original Ocean’s 11 was the first Rat Pack movie to feature all five of the group’s major players: Frank Sinatra, Dean Martin, Sammy Davis, Jr., Peter Lawford and Joey Bishop. They played a crew of World War II army veterans who plot an elaborate heist to rob five Las Vegas casinos on New Year’s Eve. Of course, the meticulously planned job that cannot fail actually does, but the crew does have fun along the way downing martinis and even singing a song or two. The five stars never really deviate from their public personas, but then again that’s not really the point: Ocean’s 11 was all style over substance, baby, and sometimes that’s just fine.
A combination of crime and romance, The Thomas Crown Affair starred Steve McQueen as a bored millionaire who tires of playing polo and golf, and decides to rob a Boston bank in order to spice things up. After pulling the seemingly perfect job, Crown is suspected by the bank’s insurance investigator (Faye Dunaway) as being the mastermind behind the job. A game of cat and mouse ensues, which turns into a full-blown affair that becomes more complicated the tighter the noose around his neck is drawn. Despite only being a modest success at the box office upon release, The Thomas Crown Affair has grown in stature over the years and was even remade in 1999 with Pierce Brosnan and Rene Russo.
This quintessential British caper is a camp classic featuring non-stop action, unbridled humor and a devil-may-care performance from star Michael Caine. Caine plays Charlie Croker, a womanizing thief fresh out of prison who plots a daring heist to hijack a shipment of gold bullion in Turin, Italy right out from under the noses of the Italian police and the mob. Employing the use of three Mini Coopers patriotically colored after the Union Jack, Croker and his crew of misfit hijackers make their escape in a planned traffic jam that sparks a climactic car chase that was one of the more humorous ever filmed. The Italian Job was remade in 2003 with American stars Mark Wahlberg, Charlize Theron, Edward Norton and Donald Sutherland.
Just before Sean Connery was seen for the last time in a long time as James Bond, he branched off to play career criminal, Duke Anderson, a recently released convict who uses mob money to finance an ambitious heist involving the wealthy tenants in an apartment building on Manhattan's East Side. What he doesn’t know, of course, is that he is being monitored by police in hopes that he will lead them to the mobsters financing the job. This fast-paced thriller from director Sidney Lumet had at its core a healthy paranoia about the use of electronic surveillance in every aspect of our lives. Keep an eye out for a young Christopher Walken, who makes his feature debut here.
Sam Peckinpah’s classic thieves-on-the-lam action thriller was gritty, violent and one of the best movies he ever made, The Wild Bunch not withstanding. Starring action hero Steven McQueen and Ali McGraw – the two began an affair during filming, much to the dismay of Paramount Pictures head, Robert Evans, who was McGraw’s husband at the time – The Getaway followed ex-con Doc McCoy and his wife Carol, who go on the run when double-crossed by a corrupt politician following a half-million dollar robbery. As they make for the Mexican border, husband and wife battle each other while trying to stay one step ahead of the law. Look out for Sally Struthers as a bored housewife who falls for Rudy (Al Lettieri), a ruthless accomplice also hunting down Doc and Carol.
Following their box office smash Butch Cassidy and the Sundance Kid, Paul Newman and Robert Redford reunited for another all-time classic. This time they played a pair of clever con artists who engage in an elaborate sting against an Irish mobster (Robert Shaw) who murdered their friend and mentor (Robert Earl Jones). Directed by George Roy Hill, The Sting featured a meticulous recreation of 1930s Chicago, witty banter between Newman and Redford, and a thrilling con that keeps you guessing right up until the end. A huge box office hit, the caper comedy was one of the most successful movies of the decade atop of earning 10 Academy Awards nominations and winning seven, including for Best Picture. Sadly, its success spawned the significantly inferior sequel, The Sting II, with Jackie Gleason and Mac Davis taking over for Newman and Redford.
Al Pacino delivered one of the best performances of his career in this late-era classic from director Sidney Lumet. Based on a real life Brooklyn bank robbery that made headlines in 1972, Dog Day Afternoon starred Pacino as Sonny Wortzik, a desperate Vietnam veteran who tries to take down a bank with his unstable partner (John Cazale) in order to pay for the sex change operation of his lover (Chris Sarandon), only to be trapped inside by police. The ensuing hostage situation devolves into a 12-hour three-ring media circus, with Sonny winning over the crowd by chastising the cops for police brutality. Both a tense standoff and a social commentary on overzealous authority, Dog Day Afternoon also boasted strong performances from Cazale, Sarandon and Charles Durning as the top cop. Nominated for six Oscars, including Best Actor, Best Director and Best Picture.