'Ocean's Eleven' turns 20: The all-time greatest heist movies – Wonderwall

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Crime has always a major subject of fascination for moviegoers, especially when a film focuses on the planning, execution and aftermath of a large robbery. There’s nothing more fulfilling than seeing a group of fictional characters attempt a heist so fantastical that it would be too hard to imagine it ever really happening. Take, for example, the all-star lineup up of George Clooney, Brad Pitt and Julia Roberts in 2001’s “Ocean’s Eleven.” The A-list trio were joined by Matt Damon, Don Cheadle, Andy Garcia, Bernie Mac, Casey Affleck, Scott Caan, Elliott Gould and Carl Reiner for the caper, which is a remake of a 1960 hit. It follows a group of con artists who plan a heist that sees them plotting to steal $160 million from three casinos owned by an incredibly wealthy businessman. It was a massive success with both critics and moviegoers that ranked on numerous outlets’ top 10 lists for the year and became one of 2001’s highest grossing films with more than $450 million in ticket sales. It came as no surprise when two sequels followed in 2004 and 2007, as well as a gender-swapped spinoff in 2018, all of which performed well at the box office. In honor of the film’s 20th anniversary on Dec. 7, 2021, Wonderwall.com is running through the all-time greatest heist movies…
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“Set It Off” broke barriers upon its release in 1996, not only for being a crime-heist film focused on an entirely female ensemble, but also because it focused on a group of Black women. Jada Pinkett, Queen Latifah, Vivica A. Fox and Kimberly Elise star as four close friends who decide to plan and execute a bank robbery to create better lives for themselves and their respective families. The low-budget flick, which earned more than $41 million in ticket sales, was praised for its quartet’s star-making performances as well as the movie’s socially conscious story. Critic Roger Ebert wrote that the film “creates a portrait of the lives of these women that’s so observant and informed… The movie surprised and moved me: I expected a routine action picture and was amazed how much I started to care about the characters.”
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1991’s “Point Break” made waves in the heist genre, literally. Keanu Reeves plays an FBI agent who goes undercover to infiltrate a gang of adrenaline junkies who are fond of skydiving and surfing– and happen to be the prime suspects behind a series of bank robberies. It isn’t long before Keanu finds himself wrapped up in the crew’s antics and develops a bond with Patrick Swayze’s charismatic leader. Oscar-winning director Kathryn Bigelow created an irresistible combination of high-octane bank-robbing and surfing scenes chock full of action, suspense and energy that raked in more than $83 million in ticket sales and has since developed a passionate cult following, with The Hollywood Reporter writing, “‘Point Break’ delivers the thrills, spills and crunches its action-hungry audience demands.”
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2011’s “Drive” quickly became a modern classic of the genre, exciting viewers with the story of an unnamed Hollywood stunt driver who moonlights as a getaway driver and falls for his neighbor, who happens to be married to a criminal. Ryan Gosling’s lead character is eventually pulled into a botched million-dollar heist that endangers the lives of everyone involved. The extremely violent film became both a box office surprise, raking in more than $80 million, and a pop culture moment thanks to its soundtrack, costumes, director Nicolas Winding Refn’s visual panache and the fantastic performances from Ryan and co-stars Carey Mulligan, Oscar Isaac, Bryan Cranston, Christina Hendricks, Ron Perlman and Albert Brooks. As USA Today wrote in its review, “The look is artfully stylized, influenced by classic film noir; the mood is dark; the performances nuanced; and the story unnervingly exciting.”

Quentin Tarantino, one of film’s most celebrated auteurs, made his feature debut with 1992’s “Reservoir Dogs.” It follows a slick-dressed crew whose planned heist of a jewelry store goes terribly wrong and depicts the planning and aftermath but skips the flawed incident itself. Harvey Keitel, Tim Roth, Steve Buscemi and Michael Madsen are excellent as some of the anonymous criminals we only get to know through colorful code names in the compelling film, which also introduces some of Quentin’s now-signature devices, such as pop culture references, extreme profanity and nonlinear storytelling. The dialogue crackles in this violent hoot, which became one of the most influential films of the era and is often regarded as a classic of independent film, with The Guardian calling it “a riveting treatise on the theme of betrayal set in an urban wasteland that murders hope and makes redemption virtually impossible.”

1995’s “Dead Presidents” took a different approach to the heist genre by jumping straight into the aftermath of an armored truck robbery and flashing back to how Larenz Tate’s former Marine ended up heading down a path of crime. In turn, it becomes much more of a character study than the usual action flick as it digs into how a group of men get to a point where they have no option but to steal a large sum of money. Directors The Hughes Brothers explore the emotional aspect of returning Vietnam veterans facing poor treatment (especially those of color) and the difficulties they endure when attempting to rejoin society. The ensemble cast includes Keith David, Chris Tucker and Freddy Rodriguez.

Acclaimed director Christopher Nolan gave the heist genre an innovative turn with 2010’s “Inception,” which stars Leonardo DiCaprio as a professional thief who steals information by infiltrating the subconscious of his targets. He’s offered a chance to have his criminal history erased as payment for the implantation of another person’s idea into a target’s subconscious and organizes a team to make the impossible mission happen. The characters in the ensemble cast that includes Ken Watanabe, Joseph Gordon-Levitt, Marion Cotillard, Elliot Page, Tom Hardy and Cillian Murphy are brilliantly sketched out and while constantly changing scenery and plot twists make it one of the most left-field crime films to ever hit theaters. Despite the confusing plot, moviegoers were won over by the jaw-dropping visuals and action, helping it gross more than $828 million worldwide, turning it into the year’s fourth biggest moneymaker. Critics were equally as smitten and it went on to win four Academy Awards.

Years before The Wachowskis changed science-fiction filmmaking forever with the blockbuster “The Matrix” franchise, they created the groundbreaking female-led crime drama “Bound” in 1996 as their feature debut. It stars Jennifer Tilly as a mafioso’s girlfriend who starts an affair with a seductive ex-con played by Gina Gershon. The pair hatch a scheme to steal $2 million in Mafia money. It was a rare move to have a genre film led by queer characters, especially one where their sexuality isn’t the plot’s focal point. Instead, it becomes a refreshing and realistic add-on to an already exhilarating pulpy heist set-up. It received positive reviews from film critics who praised the humor and style of the directors as well as the portrayal of a lesbian relationship in a mainstream film. Film critic Roger Ebert called it “one of those movies that works you up, wrings you out and leaves you gasping. It’s pure cinema, spread over several genres.”

“Ocean’s Eleven” director Steven Soderbergh returned to the heist genre in 2017 with “Logan Lucky,” which stars Channing Tatum, Adam Driver, Riley Keough and Daniel Craig. It follows an unlikely pair of brothers who plan to rob a NASCAR racetrack while avoiding security officers and the FBI, all with the help of an expert safecracker they first have to break out of prison. Brilliant performances and witty dialogue help make this a neat subversion of the usual heist movie tropes, with many critics finding the experience both charmingly clever and surprisingly stylish. Rolling Stone called it “a cool breeze of summertime sweetness that restores the good name of movie escapism.” The film also set the stage for James Bond star Daniel Craig’s more comedic turn in the theatrical hit “Knives Out” two years later.
A group of high school cheerleaders unexpectedly plan a small-town heist in the 2001 teen comedy “Sugar & Spice.” Marley Shelton and Mena Suvari star as two members of a varsity cheer squad who conspire and commit armed robbery when one of them becomes pregnant and desperate for money. The film’s characters do their research for the crime by watching numerous other heist films on this list, and in doing so, it provides a comedic and satirical take on the more action-packed entries in the genre. Coming on the heels of the massive cheerleading hit “Bring It On,” it didn’t ignite much buzz at the box office, but it has developed a cult following in the decades since among those who celebrate the movie’s dark wit and charming performances. As Variety wrote in its review, “Sugar & Spice” is “quite a smart little film with a surprising satirical edge.”
Ben Affleck marked his second directorial effort with 2010’s “The Town,” which has since become one of the most celebrated heist films in recent memory. He also stars in the picture as the leader of a group of Boston bank robbers who don nun masks and set out to get one final score by robbing Fenway Park. Rebecca Hall, Jon Hamm, Jeremy Renner and Blake Lively co-star in the blunt and brutal tale of redemption, conflict and violence. Ben’s protagonist faces a compelling struggle after becoming enamored with a bank manager he takes hostage during one of his robberies, leaving him torn between the prospect of escaping the life he’s trapped in and the childhood friends who won’t let him go. The box office hit, which grossed more than $150 million worldwide — was chosen by the National Board of Review as one of the year’s top 10 films and received both a Golden Globe and an Oscar nomination. Entertainment Weekly called it “a rich, dark, pulpy mess of entanglements that fulfills all the requirements of the genre, and is told with an ease and gusto that make the pulp tasty.”
Viola Davis, Michelle Rodriguez, Elizabeth Debicki and Cynthia Erivo took the heist genre by storm in 2018’s “Widows” as four Chicago women who attempt to steal millions from the home of a prominent local politician in order to pay back a crime boss from whom money was stolen by the women’s husbands before they were killed in a botched getaway attempt. Equal parts sparky, intelligent and timely, the film’s heroines skip the laughs and fun as they hustle to survive. It’s an excellent depiction of non-criminal characters planning a heist that also feels incredibly realistic, anchored by the winning performances from its fantastic female ensemble. “Widows” was listed on numerous critics’ top 10 lists for 2018 and earned a BAFTA Award nomination for Viola’s performance. IndieWire gave it praise for engaging “with topics as complex as sexism, police brutality, and interracial marriage,” noting “it still delivers on the car chases and gunplay. No superhero movie digs this deep.”
Robert De Niro has numerous contributions to the heist genre, including 1998’s “Ronin.” The beloved actor stars as an ex-CIA mercenary who leads a team of former special operatives hired to steal a mysterious, heavily guarded briefcase while navigating a maze of shifting loyalties. Jean Reno, Stellan Skarsgard and Sean Bean also star in the tense flick, which is set in the French cities of Nice and Paris and features a number of exciting, notable car chases that are considered some of the best in film history. Critics were impressed with the action-packed tale, with Variety saying it “reps a pleasurable throwback to the sort of gritty, low-tech international thriller that was a staple of the 1960s.”
Many consider 1950’s “The Asphalt Jungle” as the film that kick-started the heist genre. Based on the 1949 novel of the same name, it details a longtime criminal’s attempt to steal half a million dollars’ worth of precious jewels. It introduces many of the devices that have become commonplace for the movies it later influenced: a ragtag crew of specialists, the development of a big plan, an impenetrable vault and hidden security system, and the unraveling of everything as allegiances are tested. As hard-boiled and pulpy as any good noir thriller, it’s evident that heist films wouldn’t be what we know them as today without the impact of “The Asphalt Jungle.” It received four Academy Award nominations, was selected for preservation in the United States National Film Registry by the Library of Congress in 2008 and critics such as Leonard Maltin have labeled it as the best heist film ever.
2017’s “Baby Driver” took car getaway chases to a whole new level. It stars Ansel Elgort as a driver seeking freedom from a life of crime before he’s blackmailed to take part in one last job to keep his girlfriend from getting hurt. That’s when things go very, very wrong. The flick co-starring Lily James, Kevin Spacey, Jon Hamm, Eiza Gonzalez and Jamie Foxx features an onslaught of action-packed chase scenes that barely let up. Critics praised its craftsmanship and style, and the National Board of Review selected it as one of the year’s top films. It earned a substantial $226 million globally and nabbed three Academy Award nominations. Empire called it “one of the most utterly original films in years” that comes “as close to a car-chase opera as you’ll ever see on screen.”
Groundbreaking director Spike Lee tried his hat at a heist film with 2006’s “Inside Man.” It centers around an elaborate bank heist on Wall Street over a 24-hour period and features Denzel Washington as an NYPD hostage negotiator, Clive Owen as the mastermind who orchestrates the heist and Jodie Foster as a Manhattan power broker who becomes involved at the request of the bank’s founder to keep something in his safety deposit box protected from the robbers. The incredible collection of talent makes it a gripping tale full of shocking twists and turns. It was a box office smash, earning more than $184 million worldwide, and critics enjoyed the more mainstream turn from Spike. “As unexpected as some of its plot twists is the fact that this unapologetic genre movie was directed by Spike Lee, who has never sold himself as Mr. Entertainment,” Newsweek wrote. “But here it is, a Spike Lee joint that’s downright fun.”
Inspired by a 1972 robbery and hostage situation at a Chase Manhattan branch in Brooklyn, Sidney Lumet’s “Dog Day Afternoon” follows a gay Vietnam War veteran who sticks up a bank to pay for his lover’s sex-change surgery. The rag-tag criminal’s plan slowly begins to unravel and he ends up trapped in the bank while a swirling media circus gathers outside. Al Pacino stars as the amateur robber who gradually loses his marbles while trying to figure out a solution over the course of a 12-hour standoff. The heartbreaking true story is carried by the lead actor’s triumphant performance — Al makes a man who should be a villain almost impossible to not sympathize with. It became a box office hit and received nominations for six Academy Awards and seven Golden Globe Awards including best picture at both ceremonies. As Variety wrote, “‘Dog Day Afternoon’ is, in the whole as well as the parts, filmmaking at its best.” In 2009, it was deemed culturally, historically or aesthetically significant by the Library of Congress and was selected for preservation in the National Film Registry.
1999’s “The Thomas Crown Affair” is a remake of the 1968 film of the same name that replaced stars Steve McQueen and Faye Dunaway with Pierce Brosnan and Rene Russo. It’s one of the rare instances where the new version outdoes the original. It depicts a bored billionaire who starts stealing valuable works of art and is eventually pursued by an insurance investigator. Naturally, the two begin a sexy affair that also plays out like a cat-and-mouse game full of twists and turns. It became a surprise box office smash that brought in more than $124 million in ticket sales and won over critics with its winning performances and rich visual flare. As the Detroit News wrote, “Sleek and slick in equal measure, ‘The Thomas Crown Affair’ confirms that it’s well worth hearing a good story twice.”
2016’s “Hell or High Water” takes the heist genre and moves it to rural Texas. It stars Chris Pine and Ben Foster as two brothers who carry out a series of bank robberies to save their family ranch while being pursued by two Texas Rangers. The two actors give the film a ton of heart, making you care deeply for their relationship as they continue on their spree of criminal acts while sitting on opposite side of the moral compass. Film critic Richard Roeper wrote, “In ways large and small, ‘Hell or High Water’ is a movie so beautiful and harsh and elegiac and knowing, the moment it was over was the moment I wanted to see it again.” The American Film Institute selected it as one of its 10 movies of the year and it received four Academy Award nominations including best picture.
Walter Matthau stars as a detective negotiating with four gunmen who hijack a subway train and demand $1 million from the city for its release in the 1974 thriller “The Taking of Pelham One Two Three.” The standoff film veers between shocking violence, immense tension and comedy, a tonal shift that work thanks to great performances from a cast that also includes Robert Shaw, Martin Balsam and Hector Elizondo. It was a box office success and received glowing reviews, with many citing it as one of the year’s best films. The New York Times’ critic wrote that “it’s the only action picture I’ve seen this year that has a rousing plot.” It became an incredibly influential film for the genre and spawned two remakes: a television film in 1998 and another theatrical version in 2009 starring Denzel Washington and John Travolta.
Al Pacino and Robert De Niro made a long-awaited collaboration with the 1995 drama “Heat.” The formidable pair star in a story that delves deep into Los Angeles’s criminal underworld by following a detective trying to catch a seasoned criminal as he sets out to pull off his very last heist. The pair play a game of cat and mouse that lasts the entire three-hour film, culminating in the big heist and a subsequent shoot-out. It’s been cited as one of the most realistic heist films to date, one that’s told on an epic scale by director Michael Mann, who spent months shadowing the LAPD to ensure he had everything correct on screen. It grossed a noteworthy $187 million in ticket sales and received rave reviews from critics, some of whom hailed the film as a masterpiece and one of the most influential crime thrillers ever made.
Quentin Tarantino makes another appearance on the list, this time with the only film to his name that was adapted from another work: 1997’s “Jackie Brown.” Based on the 1992 novel “Rum Punch,” it revolves around a flight attendant who gets busted smuggling money and is forced to choose between keeping quiet and doing time or busting her arms dealer boss and cooperating with the police. Starring Pam Grier, Samuel L. Jackson, Robert Forster, Bridget Fonda, Michael Keaton and Robert De Niro, it pays homage to 1970s blaxploitation films like “Foxy Brown,” which also starred Pam. Reviewers were once again smitten with Quentin’s work, with Roger Ebert writing that he “leaves the hardest questions for last, hides his moves, conceals his strategies in plain view, and gives his characters dialogue that is alive, authentic and spontaneous.” It performed well at the box office and received both an Academy Award nomination and two Golden Globe Award nominations.
One of Stanley Kubrick’s earliest works of note was 1956’s “The Killing,” a suspense thriller about a veteran criminal who assembles a crew and aims to pull off a complex race track heist before retiring. It very much helps lay the groundwork for heist films to come by parsing out details of the heist bit by bit and relying on a nonlinear structure where the story is told from different people’s perspectives. It’s a lot to fit into a brisk 85-minute runtime, but it expertly introduced the revered director’s talents as a filmmaker. It didn’t make waves at the box office, but its legacy as an early standout in the genre has stood the test of time. Slant Magazine wrote that “Stanley Kubrick’s masterful manipulation of chronology brings an excruciating sense of doom to ‘The Killing,’ a classical noir about a carefully threaded heist unraveled by the scheming of a fiendish femme.”
Another remake that topped the original is 2003’s “The Italian Job,” which provided a Mini Cooper-laden update of the 1969 film of the same name. It stars Mark Wahlberg, Charlize Theron, Edward Norton, Jason Statham, Seth Green, Mos Def and Donald Sutherland and depicts a motley crew of thieves who plan to steal gold from a former associate who double-crossed them. Walking the line between fun and farce, it remains focused on stylish crimes and action-packed car chase scenes. It doesn’t have any aspirations to redefine the genre, but it does give it the sort of Hollywood popcorn-flick treatment that will delight any movie lover. As The New York Times wrote, “With its impeccable timing, steady kinetic drive and superbly choreographed chase sequences through the canals of Venice and the streets of Los Angeles, the movie, directed by F. Gary Gray, feels a like smooth, exciting whoosh down a ski slope.”
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