While not strictly a 'heist' film in the traditional sense, "The Usual Suspects" is a cornerstone of crime cinema due to its complex narrative and, arguably, one of the greatest cons ever depicted on screen – albeit one of identity. The film follows a group of criminals brought together after a failed heist and interrogated about a mysterious, legendary crime lord named Keyser Söze. Directed by Bryan Singer, the film is structured around a non-linear flashback told by the seemingly meek Verbal Kint (Kevin Spacey). The screenplay, which won an Academy Award for Christopher McQuarrie, is a masterclass in misdirection and unreliable narration. The film's impact lies in its mind-bending plot twist, which completely re-contextualizes everything you thought you knew. It's a puzzle box of a movie that rewards repeat viewings.

Sean Connery stars in this period crime film, "The First Great Train Robbery," based on Michael Crichton's novel (who also directed the movie). Set in 1855 Victorian England, it depicts a daring plan to steal gold bullion being transported by train. The film is notable for its intricate depiction of the planning and execution of the heist, requiring meticulous timing and specialized skills like lock-picking and safecracking in an era before modern technology. Crichton's background in writing thrillers is evident in the film's suspenseful structure. The movie offers a fascinating glimpse into the criminal underworld of the time and the ingenuity required to pull off a major theft without modern tools, relying instead on cunning and precise timing.

Based on the novel by Jim Thompson, "The Grifters" is a dark, neo-noir look at the lives of three interconnected con artists: a small-time hustler (John Cusack), his estranged mother who works for a crime syndicate (Anjelica Huston), and his girlfriend (Annette Bening), a seasoned grifter. Directed by Stephen Frears and produced by Martin Scorsese, the film is gritty and morally ambiguous, exploring the dangerous world they inhabit where trust is a liability. Huston received an Oscar nomination for her chilling portrayal of the manipulative Lilly Dillon. The film pulls no punches in showing the harsh realities and psychological toll of living a life built on lies and deception. It's a sharp, cynical character study within the con genre, far removed from the glamorous portrayals seen elsewhere.

"Focus" stars Will Smith as Nicky, a seasoned con artist who takes a young, aspiring grifter, Jess (Margot Robbie), under his wing. Their professional and romantic relationship complicates things as they navigate the world of high-stakes scams. The film takes you behind the curtain of various street-level cons and elaborate schemes, showing the technique and psychology involved. Smith and Robbie have undeniable chemistry, which drives the film's central dynamic. The film features scenes shot on location in places like New Orleans and Buenos Aires, adding visual flair to the proceedings. It's a sleek, modern con movie that focuses on the relationship between the con artists as much as the cons themselves, with twists designed to keep you off balance.

Rian Johnson's "The Brothers Bloom" is a quirky, whimsical tale about the last great con artist brothers, Stephen (Mark Ruffalo) and Bloom (Adrien Brody), who decide to pull off one final, elaborate con on a eccentric heiress (Rachel Weisz). The film has a fairy-tale quality to it, filled with colorful characters and unexpected turns. Ruffalo and Brody have a great brotherly dynamic, and Weisz is delightful as their unpredictable target. Johnson, who would later go on to direct films like "Knives Out" and "Star Wars: The Last Jedi," infuses the film with his signature clever plotting and witty dialogue. It's a film that plays with the audience's expectations, constantly blurring the line between the con and reality, making you wonder if anything is truly as it seems.

The 1999 remake of "The Thomas Crown Affair" stars Pierce Brosnan as a billionaire businessman who steals priceless works of art purely for the thrill, and Rene Russo as the insurance investigator tasked with catching him. This film is dripping with sophistication and features a captivating game of cat-and-mouse between the two leads, who share undeniable chemistry. The heist sequences are less about gritty realism and more about elegant planning and execution. The iconic scene where Brosnan's character attempts to steal a Monet using a diversion involving multiple men in bowler hats is a clever visual nod to René Magritte's painting 'Son of Man'. It's a stylish and romantic thriller that proves that sometimes, the biggest thrill is in the chase and the mind games.

"Now You See Me" brings together the worlds of magic and grand-scale larceny. It follows a group of illusionists known as the Four Horsemen (Jesse Eisenberg, Woody Harrelson, Isla Fisher, Dave Franco) who pull off seemingly impossible heists during their performances, sharing the spoils with their audience while being pursued by the FBI. The film's premise is built on misdirection and spectacle, much like a magic show itself. The cast is charismatic, and the film moves at a brisk pace, constantly throwing new twists and illusions at the viewer. Morgan Freeman and Mark Ruffalo add gravitas as characters trying to unravel the Horsemen's secrets. It's a fun, popcorn-friendly caper that leans heavily into the 'how did they do that?' element of both magic and movie cons.

Ridley Scott, known for epics like "Gladiator," took a turn towards a more character-driven story with "Matchstick Men," a film about phobic con artist Roy Waller (Nicolas Cage) and his protégé Frank Mercer (Sam Rockwell), whose lives are complicated by the sudden appearance of Roy's teenage daughter (Alison Lohman). Cage delivers a fascinating performance as a man struggling with severe OCD and tics while trying to pull off elaborate cons. The film delves into the psychology of con artists and the blurred lines between their professional lies and personal truths. Lohman's casting was reportedly a difficult decision, with many actresses considered, but her dynamic with Cage is central to the film's emotional core. It's a film that is as much about human connection and redemption as it is about the art of the long con.

Before the Mark Wahlberg remake, there was the classic 1969 British caper, "The Italian Job," starring the legendary Michael Caine. This film is famous for its thrilling car chases through the streets of Turin, Italy, involving a team of British criminals attempting to steal gold bullion transported in an armored car. The real stars, arguably, are the Mini Coopers used in the getaway sequence – their agility allowed for chases through pedestrian walkways and even over rooftops! The film's original ending was notoriously a cliffhanger, which remains one of the most talked-about conclusions in cinema history. It's a stylish, fun, and quintessentially British take on the heist genre, full of cheeky humor and daring stunts.

Spike Lee delivers a taut, intelligent, and utterly captivating bank heist thriller with "Inside Man." This isn't your typical smash-and-grab; it's a meticulously planned operation led by a coolly enigmatic Dalton Russell (Clive Owen), who seems to be steps ahead of the police negotiator, Detective Keith Frazier (Denzel Washington). The film is known for its non-linear narrative and sharp dialogue, keeping the audience guessing until the very end. Jodie Foster adds another layer as a high-powered fixer hired by the bank's founder. Lee masterfully uses the confined setting of the bank to build tension and explore various characters' motivations and flaws. The film's opening scene, where Owen's character breaks the fourth wall, immediately signals that you're in for something different. It's a sophisticated game of wits with a payoff you won't see coming.

Based on an unbelievable true story, Steven Spielberg's "Catch Me If You Can" stars a young Leonardo DiCaprio as Frank Abagnale Jr., a teenager who successfully conned millions of dollars by posing as a pilot, a doctor, and a lawyer, all while being chased by a determined FBI agent played by Tom Hanks. DiCaprio's performance is captivating, capturing Abagnale's audacious charm and youthful vulnerability. The film beautifully captures the look and feel of the 1960s, from the costumes to the production design. The real Frank Abagnale Jr. actually served as a consultant on the film, ensuring accuracy in the depiction of his cons, although the movie does take some creative liberties for dramatic effect. It's a thrilling cat-and-mouse chase that explores themes of identity, family, and the allure of reinvention.

Get ready for a slick, stylish, and incredibly cool heist! Steven Soderbergh's "Ocean's Eleven" is pure movie magic, bringing together an ensemble cast of the biggest stars of the early 2000s – George Clooney, Brad Pitt, Matt Damon, Julia Roberts, and many more – for a seemingly impossible casino robbery in Las Vegas. What elevates this film beyond a simple heist is the effortless charm and camaraderie of the cast; their interactions are genuinely fun to watch. Soderbergh's direction gives the film a smooth, jazzy rhythm, perfectly matching the cool confidence of the characters. Did you know the Bellagio casino, where the heist is centered, allowed the production significant access, even letting them film during operating hours? The film's success revitalized the heist genre and spawned two equally entertaining sequels, proving that sometimes, it's all about the execution and the team.

Prepare for a masterclass in cinematic deception! "The Sting" is the gold standard of con artist movies, a pitch-perfect period piece set in 1936. The dynamic duo of Paul Newman and Robert Redford, fresh off "Butch Cassidy and the Sundance Kid," absolutely crackle with chemistry as grifters plotting an elaborate revenge against a ruthless crime boss. What makes this film truly shine is its intricate plot, where layers of misdirection unfold with clockwork precision. The use of classic ragtime music, particularly Scott Joplin's 'The Entertainer' arranged by Marvin Hamlisch, became synonymous with the movie's playful, cunning spirit and won an Oscar. It's a film that demands your attention, constantly making you question what's real and what's part of the long con. Winning Best Picture at the Oscars, it cemented its place in film history as one of the most entertaining and cleverly constructed capers ever made.