When factoring in the punishment, a lengthy prison sentence should be a strong deterrent for five-finger discounts. Every cinematic crook has a price tag tied to the level of risk they’re willing to ignore in heist films.
In some cases, characters in caper films have been robbed for personal reasons, making it difficult for audiences to empathize with their risk tolerance during the robberies. Viewers can be swayed when the arithmetic justifies the crime, and lofty payouts are associated with the heist.
'Thomas Crown Affair' (1999)
Billionaire, playboy, and philanthropist Thomas Crown (Pierce Brosnan) is a kleptomaniac and passes the time by stealing priceless works of art. An insurance investigator detects his vice, but his sleight of hand is deceptive enough to allow him to slip away with the "San Giorgio Maggiore at Dusk" painting by Oscar-Claude Monet.
Crown is motivated by his elusiveness and toys with the detectives during the chase. He steals the Monet, valued at $100 million, and returns it within hours of his theft. At the film's close, Crown steals a more affordable piece of art, "The Banks of the Seine at Argenteuil" by Edouard Manet, estimated at $65 million.
'Fast Five' (2011)
Before the events of Fast Five, Vin Diesel’s character mainly operated in the realm of street racing. The funds locked up in the vault from the fifth installment were enough to persuade Dominic Toretto (Diesel) and his crew to shift focus and plan an elaborate heist.
Torretto recruits a team comprised of members from each of the previous installments of the Fast and the Furious series. Dom always finds a way to make it a family affair, so the $100 million stolen from the merciless drug lord is split evenly between seven Fast Family members.
'Ocean’s Eleven' (2001)
Recently released Danny Ocean, played by George Clooney, opts out of being a contributing member of society and assembles a team of thieves to rob his ex-wife’s new boyfriend in Ocean's Eleven. The target for the theft Terry Benedict (Andy Garcia), is the owner of three lucrative Vegas casinos.
By law, on a fight night, Benedict’s casinos are required to carry north of $150 million in cash and coin, and this obligation entices Danny and his team to go for the vault during a heavyweight bout. The actual losses suffered by Benedict were $163,156,759 and his girlfriend and Ocean's ex, Tess (Julia Roberts).
'Triple Frontier' (2019)
Led by Oscar Isaac and Ben Affleck as Pope and Redfly, a group of ex-Delta Force operators has problems adjusting to civilian life and figure their transition could be easier if finances weren’t a concern. The team plans to break into a South American drug lord’s compound to fund their nest egg.
The squad expected to amass $75 million in the cartel boss’ hidden mansion, but after finding stashes of money hidden in the walls, the team departed from the estate with $250 million in duffle bags. The robbery was successful, but the less-than-stellar getaway involved the soldiers literally burning through cash as they struggle to survive the element en route towards their cold journey home.
'Ocean’s 8'
A spin-off from the Ocean’s trilogy, Ocean’s 8 features an all-female cast of con artists. Following her big brother’s footsteps, Debbie Ocean (Sandra Bullock) assembles a team of female felons to steal a blinding cascade of diamonds by Cartier, dubbed the Toussaint.
The Toussaint necklace in the film was worth $150 million. The lawbreakers successfully stole the necklace and deposited the earnings into Ocean’s ex-boyfriend’s account to frame him. The necklace heist was a diversion, and the crew slipped away with jewels from a museum that allowed each member to pocket $38.3 million from a total take of $306,400,000.
'Now You See Me' (2013)
The Four Horseman is a group of magicians brought together by a rogue FBI agent, Dylan Rhodes, played by Mark Ruffalo. The blameless magicians in Now You See Me give away 100% of the funds they steal. Under Rhodes' leadership, the Four Horseman square off with the FBI in a three-act face-off involving three separate heists.
Rhodes' father was a disgraced magician who fell victim to a defective vault during a magic trick. After the insurance company refused to pay the family the payout following the accident, Rhodes devised three vengeful heists as a form of payback to the bank, the insurance company owner, and the vault manufacturer, and the earnings from the robberies were €3 million $140 million and half a billion respectively.
'Ocean’s Thirteen' (2007)
Danny Ocean’s attempt to turn a new leaf is interrupted when a casino owner Willy Bank, played by Al Pacino, provokes Danny and his ensemble by threatening a teammate. Ocean’s team joins forces with their arch-enemy Benedict to rob the new target in.
Danny Ocean and his crew walked away with their highest payday in Ocean’s Thirteen. In the span of three minutes and twenty seconds, Ocean and his accomplices stole $500 million from Bank's casino and mugged him of his sentimentally valued diamond necklaces worth $250 million.
'Entrapment' (1999)
Opposites attract when an insurance investigator courts a professional thief for a series of heists in Entrapment. Although worried each teammate has plans to entrap the other, both Catherine Zeta-Jones' character Gin and Sean Connery's character Mac employs nonexistent risk aversion when they discuss a plan to rob the International Clearance Bank.
Gin informs Mac about her plan to steal $8 billion from the Bank of International Settlements in Malaysia. It’s revealed later in the movie that Mac is a double agent and has been working with the FBI to catch Gin; however, you should never trust a thief. Mac stole $8 billion, and when prompted to the funds by the FBI, he returns only $7 billion back allowing him and his love interest to sail into the sunset with the missing balance.
'Dark Knight' (2008)
The Joker (Heath Ledger) ruffles the feathers of the mob as he robs mafia-owned banks in Gotham City. In addition to the money he’s stolen, Joker confiscates the piles of cash the mob's accountant hid for safekeeping to protect the criminals from RICO charges.
There aren't enough hours in a day to count the pallets of currency by pressing pause during Joker's Scrooge-esque dive from the top of the stack of cash in The Dark Knight flaming money scene. Joker sets the entire pile of money ablaze in the blink of an eye. Luckily, Esquire has estimated that the pallets house 5.832 million cubic inches suggesting Joker's robbery rendered approximately $6.328 billion and made him the second-richest person in Gotham before his net worth burst into flames.
'Die Hard with a Vengeance' (1995)
In the third installment of the Die Hard series, the past comes back to haunt John McClane (Bruce Willis) after Simon Gruber (Jeremy Irons) torments the detective to avenge the death of his older brother Hans Gruber (Alan Rickman) from Die Hard. Gruber orchestrates a series of terrorist attacks around New York to lure the police away from Wall Street so he and his goons can rob the Federal Reserve Bank of New York.
Gruber's bankable game of Simon Says results in fourteen dump trucks hightailing $140 billion worth of gold bars from the Federal Reserve to the Canadian border. Gruber is successful in pulling off the 520-mile expedition and evading the NYPD. The relentless McClane has to enlist the support of the Royal Canadian Mounted Police Department to bring Simon to justice.