Here it is—the other half of our endeavor to evaluate movies about large-scale theft! This is the accompanying list to our recently released ranking of the 50 most iconic Heist movies. We wrote at the start of the Heists list, “We will be releasing an accompanying list of the Best Capers shortly after this one, so if you don’t see a film with a great heist in it, keep your shirts on, because it’s probably on the other list” and this is that list. Ta-da. These two lists were written at the same time, so this is not some sort of amendment to the first list. It is the other half you’ve been waiting for!
Why are there two lists? Because the Caper is a sub-genre of the Heist film with its own specific rules and mood. Looking at each category of films (Heist versus Caper) specifically allows for more thoughtful ranking experience, between them. The Caper sub-genre features films which are (overall) lighter and wittier than the standard Heist movie. While characters in Capers also frequently pursue large sums of shadily-acquired money or other items of value, these films are not necessarily about the acts of committing robberies, as Heist films always are. This is important, so I’ll repeat it: for a film to be a heist movie, items have to be literally stolen. In a caper, items may be stolen, but they don’t have to be; there can be swindling and cons and money-laundering and other forms of theft. Not all con movies are capers. For example The Hustler is not on here, nor is Fabián Bielinsky’s Nine Queens, perfect examples of “Con” movies that are neither Heist nor Caper.
Keeping our rankings as streamlined as possible according to these two categories helps to compare them; what’s the point of ranking excellent comedies and excellent tragedies next to one another if you’re straining to find shared ground to complete your comparative assessment? This is why this effort has always been a two-part undertaking.
What else really makes a Caper different from a Heist? Unlike the traditional Heist movie, which is usually a slick, deft, high-octane practicum, a Caper can be madcap, zany, as well as, on a different note, extremely romantic or flirty. The Caper is where you’ll find clever banter, silly sidekicks, gags, slapstick, and things generally going hilariously wrong. It’s also where you’ll find, more often than not, men in well-fitting suits who can’t be trusted or other sexy cat burglars, and tons of romantic tension. These movies are hardly gritty, they’re frequently not about the underworld. If they are, they’re funny as a result. Generally speaking, in terms of tone, if the Heist is a stomp, than the Caper is a romp.
When a movie is remade, sometimes it will move from Heist territory into Caper territory, or vice versa. Remakes like The Ladykillers, The Italian Job, and The Thomas Crown Affair occupy different categories than their originals and are therefore on different lists. As with the Heists list, keep in mind the criteria we’re using: we’re looking at the most iconic movies in this category, and we are ranking them from “worst” to “best.”
Please note: The Pink Panther movies are deliberately not on this list. This list focuses on capers from the perspective of those embroiled in schemes, not the detectives on their cases.
So, with all that clarified, let’s settle this.
35. The Hustle (2019)
It would have been a huge relief if The Hustle, a female-led con movie starring Anne Hathaway and Rebel Wilson were any good, but it’s really, really not. I want the best for both of them, but that’s far from what this movie has in store. I am generally wary of any film which promises “taking down men” as its contribution to feminism. I prefer my feminism not to be so cheap, or such a sham.
34. The Sting II (1983)
I’ll never understand how anyone green-lit this film, but since someone did, here goes. Jackie Gleason (a genius performer, but why star in this movie except to ride Minnesota Fats’ coattails?) plays a con man named Fargo Gondorff (no relation to Newman’s Henry) and Mac Davis plays his mentee, Jake Hooker (no relation to Robert Redford’s Johnny). They decide to make a fortune rigging a boxing match, but things don’t go according to plan. Rounding out the most baffling cast ever are Teri Garr, Oliver Reed, and Karl Malden. Despite being written by David S. Ward, who wrote the original, it is almost unwatchably bad.
33. Gambit (2012)
It’s a shame that this silly adaptation of Ronald Neame’s Gambit is so lackluster, especially since its script was written by the Coen Brothers and it stars Alan Rickman as its villain. Colin Firth is an art curator who tries to dupe his boss into buying a fake Monet, and he needs rodeo queen Cameron Diaz’s help for some reason. The movie plods and the jokes rarely land, but by Jove does surprise sidekick Tom Courtenay, playing a daffy British army man, steal the show.
32. Big Deal After Twenty Years (1985)
This sequel to Fiasco in Milan doesn’t live up to the second and definitely doesn’t live up the first, although it does at least attempt to do something new, rather than repeat the success of the first film. In this third chapter, Marcello Mastroianni is now the main character, fresh out of prison and reuiniting with his old friends from the gang, Peppe (our hero from the last two movies) and Michele.
31. Going in Style (2017)
Zach Braff directs this superfluous remake of the classic 1979 comedy, which now stars Morgan Freeman, Michael Caine, and Alan Arkin as three old men who attempt to rob the bank that screwed them over. I don’t know why this film needed to be made, but it was, but there’s a host of elderly actors it’s nice to check in on, from Ann-Margaret to Christopher Lloyd. The best moment is when Morgan Freeman sits in the basket of a motor-scotor Michael Caine has stolen.
30. Fiasco in Milan (1959)
This sequel to Big Deal on Madonna Street sets our favorite band of thieves (still led by Il Mattatore!) after a big-time heist. This time, they have to steal a suitcase of money (containing the pool of bets over soccer tournaments). As you might expect with these guys, though, things don’t go acording to plan. Unfortunately, the sequel is nowhere near as good as the first, but hey, Claudia Cardinale is in this one!
29. Gambit (1966)
Michael Caine and Shirley MacLaine star in this film from cinematographer-director Ronald Neame, about a cat burglar who needs an exotic dancer to impersonate the dead wife of a wealthy mark. This film would be a lot funnier/better without its other-ism/exoticism/orientalism and of course if Shirley MacLaine were not in yellowface, playing a mixed-race woman named Nicole Chang.
28. Quick Change (1980)
This rather obscure 80s comedy begins with Bill Murray dressed as a clown, attempting to rob a bank. What seems to start off as a joke turns into an extraordinarily successful robbery. But robbing the bank, which he does with his girlfriend Geena Davis and his best friend Randy Quaid, turns out to be easy compared to what’s left: fleeing the city and successfully absconding with the cash. It’s not even that Jason Robards, the weary chief of the NYPD, is hot on their tail; it’s that it’s impossible to get to the airport in New York City in a reasonable amount of time. This movie is fascinating because it’s so frustrated, so fed up with NYC; despite its absurdity, it’s strangely identifiable for those of us who’ve been in this city for too long without getting away.
27. Rat Race (2001)
Rat Race is a millennium-era chase film with an all-star cast that Book Marks editor Dan Sheehan paid money to see in theaters. It’s kind of a reboot of It’s a Mad Mad Mad Mad World, in which John Cleese is a casino tycoon who initiates a giant competition with a promised fortune at the end. There’s a Barbie Museum, a hijacking of Hitler’s car, and a cast which includes Rowan Atkinson, Whoopi Goldberg, Breckin Meyer, Amy Smart, Cuba Gooding Jr., Jon Lovitz, and Seth Green, a group of people with this movie and “2001” in common, and nothing else. It is, though, very fun. Also, I’m shocked that Michael Caine is not in this movie.
26. The Truth About Charlie (2002)
I wish this remake of Charade, starring Thandie Newton and Mark Whalberg, lived up to what Thandie Newton deserves from this world, but it doesn’t. Cameos include Agnes Varda and Anna Karina, and those are very charming.
25. Entrapment (1999)
I’ll talk a lot about age differences in romantic capers when we get to Donen and Hitchcock, but it’s worth mentioning the strangeness of Entrapment‘s casting thirty-year-old Catherine Zeta-Jones and sixty-nine-year-old Sean Connery as romantic leads (their *thirty-nine-year* age difference makes the twenty-five year age difference between Zeta-Jones and her actual husband Michael Douglas seem negligible). But anyway, Connery is an art thief and Zeta-Jones is the insurance agent sent to hunt him down. If you’re looking for a movie that lays the seduction on really thick, you should watch it. It’s got a masked gala, Catherine Zeta-Jones elastically weaving her body through a net of lasers, and that ubiquitous scene where a man puts a giant jewel around a woman’s neck from the back and she stares at the whole scene through a mirror and imagines what her life could be like.
24. Going in Style (1979)
I love when famed acting coach Lee Strasberg acts in movies. He’s not in many, but I love it every time. His voice is so odd, so intriguing. And he’s the third guy in this comedy, about three elderly men who attempt to rob a bank (the other two geezers are Art Carney and George Burns, both of whom I also love). This is a charming movie; the humor is simple but perfectly executed, like the scene where the men are all trying to find the correct-sized bullets to load into their guns and are sitting around a kitchen table together, loading over and over again. George Burns can make any line funny, Art Carney is fabulous at restlessness, and Lee Strasberg can look nervous like no one you’ve ever seen.
23. The Great Muppet Caper (1981)
The Great Muppet Caper is the most charming film on this list. In this adventure, Kermit, Fozzie Bear, and the Great Gonzo are all disgraced reporters, fired from their newspaper for failing to break a story about a jewel heist that happens during the opening musical number, when they are standing right there. So, the trio fly to London, to try to grab a story, just the same, hoping to interview the woman, Lady Holiday (Diana Rigg), who has been robbed. She is a fashion designer, planning to unveil her new collection. But she’s also the unwitting target of thieves who, now that they’ve stolen one set of her jewels, won’t stop until they grab them all. The ringleader of this gang is her own brother, Nicky (national treasure Charles Grodin), who has fallen in love with Miss Piggy, an aspiring model who winds up impersonating Lady Holliday because she wants to impress Kermit. There are delightful musical numbers, charming cameos, and Muppets. Muppets everywhere. It’s a hoot.
22. The Brothers Bloom (2008)
In this charming, offbeat adventure movie written and directed by Rian Johnson, Mark Ruffalo and Adrien Brody are brothers and con-men out for One Last Job, one that requires them targeting eccentric, lonely heiress Rachel Weitz and bringing her on a trip around the world. The plan involves faking their deaths and absconding with $2.5 million of her money while she flees pursuers who don’t technically exist. But she’s a lot smarter than they expect, and the adventure takes lots of turns for the surprising. It’s an enjoyable, clever movie that slips on different genre conventions at different times. Then again, Rachel Weisz all alone in her sprawling mansion, slightly crazy and learning tons of unconventional hobbies, might hit a little too close to home for us all, after spending months of quarantine.
21. Dirty Rotten Scoundrels (1988)
Michael Caine and Steve Martin are two rival con men in a race to see who can swindle an American heiress out of her fortune, in this rollicking comedy set along the French Rivera. Apocryphally, David Bowie and Mick Jagger were supposed to star in this movie which would have been… a different film entirely. A classic: put it on and you’ll put on the ritz.
20. Charade (1963)
I’m not the world’s biggest fan of Charade, as much as I am often entertained by many Stanley Donen movies. Maybe it’s because I’ve just never gotten the appeal of late-career Cary Grant or because Charade is too slow for a film whose Saul-Bass-designed credit sequence promised would twist and whip along. If I enjoy it, I enjoy it for the presence of James Coburn and especially for the casting of Walter Matthau as an exhausted, sardonic American bureaucrat stuck in Paris, but anyway… Audrey Hepburn is about to divorce her husband when she finds out he’s been murdered. Turns out, he was CIA, but more than that—he was part of a group who secretly stashed stolen money during WWII, and after he dies, all his old buddies assume Audrey Hepburn knows the actual location of the treasure, and come after her. George Kennedy chews the scenery nicely as one of these visitors, a loud assassin with a hook for a hand.
19. To Catch a Thief (1955)
Cary Grant again—not as old or as silver-haired as he is in Charade, but definitely up there. He’s fifty-one. Fifty-one and dating twenty-six-year-old Grace Kelly. (It’s actually the same twenty-five-year age difference as in Charade, since Audrey and Grace were both born in ’29 but Thief‘s 51-26 age difference seems worse somehow than Charade‘s 34-59 age difference. IDK.) Anyway, ignoring this bit of unpleasantness yields a very enjoyable viewing experience. To Catch a Thief is a fun and very flirty Hitchcock movie, in which former jewel thief Cary Grant is enjoying his retirement on the French Riviera, until he is suspected to be up to his old tricks when some wealthy tourists’ valuables go missing. But Grace Kelly really steals the show, here (even over the verdant scenery, putting VistaVision and Technicolor hard at work). Her character, Frances, gleefully, totally lusts over Cary Grant, planning her capture of him just as methodically as she plans how to help clear his name (you don’t bring chicken on a picnic unless you’re planning to deliver some heavy double-entendres). For all this movie’s interest in diamonds, there’s nothing cold about it; To Catch a Thief is about flesh.
18. A Fish Called Wanda (1988)
Kevin Kline won his Best Supporting Actor Oscar for playing Otto, the Nietzsche-reading, Aristotle-misunderstanding, gun-wielding, armpit-smelling Ugly American who eventually becomes the villain of this movie, but the whole thing is a comic masterpiece. It’s about four people (Jamie Lee Curtis, Michael Palin, Kevin Kline, and Tom Georgeson) who attempt to pull off a bank heist but wind up devising their own schemes to nab the loot and get off scot-free when one of their gang members is arrested. Jamie Lee Curtis decides to try to seduce John Cleese, the lawyer working on the case, but this also causes more problems than it solves, especially because her boyfriend Kevin Kline is too dull and jealous to look at the big picture. Michael Palin is adorable as an animal-loving assassin, but the film sets up a lot of laughs based on his speech impediment, a stutter, and this is the only part of this movie that isn’t cool.
17. Heist (2001)
Despite the word “heist” in its name, this film, written and directed by David Mamet, rings more as a caper to me, because it follows the exploits of one man as he slickly out-maneuvers the crooks who offer him a bad deal, it’s characters are caricatures, it’s full of romantic intrigue, and it also frequently pastiches heist films. Most David Mamet-written things play with audience expectations, and so does this one; it’s a witty, slippery film that’s half a heist and half an outfoxing. Maybe the funnier threads in here are most clearly due to the presence of Danny DeVito, who provides ample comic relief even when he’s serious, but also because (this is a Mamet script, after all), it is so self-referential, so self-knowing that all its action feels like a playful experiment even when it’s breakneck or grave. This might be a controversial ranking, but lists like these are supposed to be fun, so whatever. Also, Delroy Lindo doesn’t get enough praise.
16. Fantastic Mr. Fox (2009)
This beautiful stop-motion Wes Anderson adaptation plays fast and loose with its classic Roald Dahl source text, but it nonetheless makes for a sublime caper. The suave Mr. Fox (voiced by George Clooney), a newspaper columnist, has long given up his former life of thieving, running, and hiding. But eventually, he slips back into his old ways, stealing food from three surly and threatening farmers.
15. The Hot Rock (1972)
I always, always enjoy The Hot Rock, a clever caper written by my favorite screenwriter William Goldman, based on the novel by Donald E. Westlake (in his Dortmunder series). It stars Robert Redford and is about a group of thieves who try to steal a diamond from a museum… but things don’t go according to plan, so they wind up having to steal it four times. A delight.
14. It’s a Mad, Mad, Mad, Mad World (1963)
I first watched It’s a Mad, Mad, Mad, Mad World with my grandfather when I was five years old, so it would have a special place in my heart even if I didn’t admire it as a tremendous filmmaking achievement. When Jimmy Durante dies in a roadside (cliffside, really) car accident on his way to collect long-buried money, he tells, with his dying breath, the location of this great treasure (buried underneath “a big W”) to the eight bystanders who stop to help. As they desperately race across California to try to beat one another to the money (accruing more and more participants as they go), they become embroiled in terrible jams and petty crimes along the way (all without knowing a police squad is on their trail). The cast (from main actors to tiny cameos) is a who’s-who of the midcentury’s greatest performers, from huge stars to veteran character actors. I can’t decide who I love more, Terry-Thomas or Phil Silvers; it’s a close call, but I do have a large black-and-white photo of Terry-Thomas in my living room.
13. Judex (1963)
This elegant, complicated French caper, directed by Georges Franju, stars American magician Channing Pollock as Judex, a masked avenger-vigilante who blackmails a wealthy, unscrupulous banker but must sidestep these plans when the family’s former governess kidnaps the banker’s virtuous daughter Jacqueline in an attempt to ransom her. Robert Giordani’s art direction and Marcel Fradetal’s cinematography make the film extra special—every scene glitters and twinkles. But the best part of the film is the costume ball scene, when Judex and Jacqueline show up in elaborate bird masks.
12. Snatch (2000)
Guy Ritchie’s Snatch is even more lighthearted than his debut Lock, Stock, and Two Smoking Barrels (plus it’s more of a chaotic chase film than a proper heist), so we put it here. It’s about several disparate groups of people who attempt to track down a stolen diamond, taken from Frankie Four-Fingers (Benicio Del Toro). Brad Pitt stars as Mickey, an Irish Gypsy boxer with an unintelligible accent, and Jason Statham is Turkish, an unlicensed boxing promoter whose story gets yanked into the tale of the hunt for the diamond by several parties, including one group of Americans led by an especially brash Dennis Farina, who really shines through it all.
11. The Thomas Crown Affair (1999)
This remake of The Thomas Crown Affair ditches its predecessors grasp on neo-noir and swaps it out for sexy intrigue. One of two art-theft-related romantic suspense movies to come out in 1999, Thomas Crowne stars Pierce Brosnan as a wealthy playboy who steals art for fun, and Rene Russo as the cunning detective on his case. It’s suave and sexy without being too heavy. It’s actually probably the perfect film to watch right now. Such an escape.
10. The Ladykillers (1955)
Alec Guinness leads a talented cast (which includes Peter Sellers) in this farcical crime story, about a group of five criminals who rent rooms in a charming London abode from an elderly widow named Mrs. Wilberforce. They need the spot to commit a burglary, but they pretend to be classical musicians. As someone who specializes in the history of Victorian entertainment I find this movie especially fascinating; Mrs. Wilberforce is a persistent holdover from the Victorian era, and underneath its crime story, the movie is partially a culture-clash tale between the modern era, and an antiquated one. But it’s extraordinarily funny, too. And Alec Guinness is wonderfully creepy.
9. Out of Sight (1998)
In this Steven Soderbergh film, George Clooney (at peak George Clooney) is a bank robber who escapes from prison and J-Lo (at peak J-Lo) is a U.S. Marshal he winds up having to kidnap in order to make his escape. Once she’s free, she’ll pursue him, with the help of her knowing U.S. Marshal dad Dennis Farina. But in the moments they have together, they discover an intense mutual attraction that makes it a lot harder for them both to pursue what they want. I think this is the best of the “pursuer/pursued romances” on this list; plus the chemistry between Clooney and J-Lo is absolutely insane. Absolutely electric. Even possibly more electric than Pierce and Rene, and I can assure you that we don’t throw this sentiment around lightly.
8. The Lavender Hill Mob (1951)
In this Academy Award screenplay winner, Alec Guinness star as a shy bank transfer agent who dreams of being rich. When he befriends Stanley Holloway, an eccentric souvenir-maker, they decide to rob the bank where Guinness has dutifully worked for two decades, facilitating the transfer of gold bullion. They devise a plan to smelt the gold into figurines and smuggle them to France. But they’re going to need help, so they pretend to be tough-guys and enlist the help of two criminals, forming a bank robbing gang for the ages. This is a “watch with your best friend” kind of movie. A lovely time.
7. Big Deal on Madonna Street (1958)
Mario Monicelli directs a crack cast in this wonderful Italian caper which stole my heart. Spoofing Rififi a little bit, it’s a perfect gem of a comedy—Vittorio Gassman, Italy’s “Il Mattatore,” is a petty crook with dreams of being a big-time thief, who plans a perfect pawnshop heist on a quiet block in Rome. But once word gets out about his plot, all manner of unscrupulous characters come out of the woodwork and hope to take part in it. It’s an ensemble cast like you’ve never seen before.
6. Raising Arizona (1987)
In this second feature from the Coen Brothers, Nicolas Cage gives the best performance of his career, as H.I., a pathetic petty thief who attempts to go straight when he falls for Holly Hunter’s Ed, the police officer who processes his arrest. They fall in love and get married, but find that they are unable to have a baby. So they plan to steal Nathan Jr., one of the newborn Arizona Quintuplets, babies recently born to local furniture sales magnate Nathan Arizona. But love, guilt, petty thievery, and a leather-clad, motorcycle-riding bounty hunter get in the way.
5. Catch Me If You Can (2002)
Leonardo DiCaprio and Tom Hanks are teenaged con man/forger Frank Abignale Jr., and uptight FBI agent Carl Hanratty (respectively) in this perfect cat-and-mouse caper from Steven Spielberg, which is equal parts fun and devastating. Tom Hanks is overdoing it on the Boston accent, yes, but once you get past that, the relationship between hunter and hunted becomes almost as enjoyable as watching young Frank slip in and out of various snags. Also, why Christopher Walken didn’t win an Oscar for Supporting Actor is beyond me. Must have slipped right off his neck. (Actually, I confess, it’s not beyond me… that category was insane that year! Paul Newman for Road to Perdition? Chris Cooper in Adaptation? Ed Harris in The Hours? John C. Reily in Chicago? I just really wanted to make that joke.)
4. Topkapi (1964)
Peter Ustinov deservedly won the Academy Award for Best Supporting Actor in this joyous, glittering, clattering thriller about a motley group of thieves and one con man who steal a priceless, emerald-encrusted dagger from a museum. I don’t know that I’m the world’s biggest Melina Mercouri fan, but I do love that this heist is helmed by a badass woman who does whatever she wants. And she wants to steal emeralds.
3. The Italian Job (1969)
Do you like watching expensive cars tumble down the sides of cliffs? Well, then The Italian Job is for you, because it does this like seven times. The movie is a jubilant, high-stakes caper with a crack cast and incredible stunts. Michael Caine stars as Charlie Croker, a wealthy crook, recently released from prison, who receives a transmission from his recently-deceased mentor containing the plans for the perfect heist. He vows to pull it off. It involves causing a traffic jam in the city of Turin that will allow the theft of gold bars from a van. Croker does need Noël Coward, a very British gangster who’s still locked up (comfortably), to help finance it. It’s a grand old time, with a gorgeous color palette. It’s worth noting, though, that it is fairly dated in its casual misogyny… I don’t have the space to get into all the reasons but let me just say that one of the essential crew members is Benny Hill, a computer science professor on leave from his post and staying in the psych ward because he is actually a sex offender. He has an unstoppable urge to grab the behinds of plus-sized, older women, but Croker sets him loose for their scheme anyway, meaning he gets to run some havoc around Italy, and this is supposed to be comedy but it drove my blood pressure higher than the scene in which the mini coopers drive onto that giant convex concrete roof. But other than this, the scheme is clever, the car chases are amazing, and the ending is very amusing. It didn’t exactly “blow the bloody doors off” for me, but it came bloody close.
2. How to Steal a Million (1966)
Audrey Hepburn and Peter O’Toole light up the screen in this perfect little caper, about a young Parisian woman who disapproves of her jolly father Hugh Griffith’s penchant for art forgery. He’s an impeccable imitator of the Great Masters, and makes a pretty penny from selling them, but when he loans a priceless statue forged by his own father to a museum for an exhibition, he finds out that the statue will have to be examined in order for it to be given its mandatory $1 million insurance protection. Knowing that an examination will expose her family’s history of art crime, Audrey decides to steal it back from the museum, somehow. Only, since she has had no interest in a criminal lifestyle until now, needs to enlist the help of sexy cat burglar Peter O’Toole to help. The heist they pull off is one of the cleverest ones I’ve seen onscreen. And the scene where Audrey Hepburn sees Peter O’Toole for the first time, when he’s peeking out at her over the frame of the painting he’s swiping, and his eyes are super blue and when he puts it down it’s revealed he’s wearing a tuxedo… no better meet-cute in the history of cinema.
1. The Sting (1973)
At CrimeReads, we worship the king and accept no substitutes. Robert Redford is a young grifter who, out for revenge against powerful crime boss Robert Shaw (just two years before his turn in Jaws, and there’s nothing grizzled about him here!), heads to Chicago to learn the Big Con from the once-great flimflam man Henry Gondorff, played by Paul Newman. Together they pull together a team for the greatest con in cinema history. This film manages to both draw its audience in and keep it at arms’ length, a combination that allows the twists to keep unfurling even while you feel like you’ve got skin in the game.
