Although I love traditional mysteries with their law abiding, law enforcing heroes and heroines, I admit to having a soft spot for the crime stories that flip the hero paradigm around and put the law breakers into the spotlight. Still under the umbrella of crime fiction, these stories focus on the successful achievement of a criminal undertaking rather than preventing a crime or catching the criminal. Charming rogues, loveable rulebreakers, and morally ambiguous anti-heroes are my catnip. In both capers and heists, much of the appeal is related to characters. You have to like these characters (or at least be interested by them) in order to follow them to the dark side. It helps that the characters in a caper or heist is often funny and smarter than everyone around them. The other big appeal is plot, of course, as they tend to be intricately planned schemes that reward careful attention and showcase the clever ingenuity of the lawbreakers. Two overlapping stories that explore stories that flirt with (or fully embrace) the criminal side of the mystery line are capers and heist stories.
Capers
The key characteristic of the caper novel is the inclusion of humor. Often featuring appealing thieves, or at least characters whose loyalties or law-abiding nature is in doubt. The crime in a caper novel is not usually a mystery — you see the crime play out, usually know all the players, and the fun is watching it (the caper) get planned and executed and root for your crook to get away with their criminal undertaking. Not particularly violent in nature and rarely including a dead body, the crime your anti-heroes are trying to get away with is usually thievery, but often with an audacious and ambitious execution.
Heists
Closely related, the heist story is also one of organized thievery, but usually with an emphasis on assembling a team of skilled and larcenous characters who must work together to achieve their goal. Although it can have the lighthearted humorous tone of the caper, it can be more serious and gritty in tone as well. They also usually have a hefty dose of the tension of a thriller, as the reader is on the edge of their seat, anxious to see if the team can successfully carry out the heist.
There are so many excellent stories being told with either the caper attitude and/or the heist structure that I actually thought I’d better split them up into a few posts. Today, I’ll pick some of my favorite films, as movies were some of the earliest places I encountered these stories and remain a favorite genre. I”ll follow up a post with crime novels (including a few romantic capers) and finish up with SF and Fantasy capers.
So let’s talk heist and caper movies! I’m going to list some of my personal favorites in sort of a dark to light order. As I said, some are tense, almost noirish thrillers and then there are some light farcical capers with romance and/or humor. I appreciate both moods, although I will admit that some of my all-time, most-watched favorites are on the lighter end.
Rififi 
(directed by Jules Dassin)
If you wanted to just pick one example of the heist movie to represent the genre, this would be a good choice. Yes, it is black and white. Yes it is subtitled French. But for the noir end of the heist genre, this is dark and incredibly suspenseful, with amazing performances (especially from Jean Servais as Tony). The basic plot is as follows: Tony le Stephanois gets out of prison, meets up with old friends and pretty much immediately falls back into old patterns. He and his four man crew decide to rob a high-end jewelry store. Not a slick or glamorous heist like some movies in the genre – this is grittier. And the heist itself! Dassin doesn’t stint in showing the planning (often an entertaining part of any heist story) and the robbery itself is such a nail-biter that I get tense just thinking about it. Interesting backstory is that Dassin was an American filmmaker blacklisted in the McCarthy era who moved to Europe and went on to great success. He also directed Topkapi
Sexy Beast
(directed by Jonathan Glazer)
When I tell you that this stars Ray Winstone, Ian McShane and Ben Kingsley, maybe I don’t have to mention the unbelieveably inventive amount of cursing? Winstone is Gal, an ex-con retired to a villa in sunny Spain who gets a visit from Don Logan (Kingsley), an old criminal associate who wants his help on a bank heist. Gal refuses, Don insists and there is a truly amazing battle of wits between the two. I won’t give too much more away, except to say that Kingsley’s performance has to be seen — he’s brutal and completely fricking crazy but you won’t be able to take your eyes off him. Very un-Gandhi. The heist later in the film is great too, but this is more of a portrait of these criminals. There’s a good dose of dark humor amid all the violence, too.
Bob le Flambeur
(directed by Jean-Pierre Melville)
I promise they won’t all be in French, but this is another absolute classic of the genre. It’s about Bob (le Flambeur is “the Gambler” or “the high-roller’) an aging ex-con and unrepentant gambler played by Roger Duchesne. He’s been on a losing streak for a while, coasting on his charm and the good will of friends when he hears about a huge reserve of cash sitting around at the Deauville casino. He plans his heist, all while taking a young streetwalker in under his wing. Melville’s movies are always stylish, usually with super-cool heroes (he also directed Le Samourai
The Thomas Crown Affair
– 1968 (directed by Norman Jewison / The Thomas Crown Affair
– 1999 (directed by John McTeirnan)
The original has Steve McQueen and Faye Dunaway, the remake Pierce Brosnan and Rene Russo. They both are about a charming millionaire named Thomas Crown who pulls off the perfect crime (theft of a huge amount of cash in the first film, and a priceless painting in the second) as a kind of game, only to attract the attention of attractive insurance investigator (Vicki Anderson in the older version, Catherine Banning in the new). Crown and the investigator dance with attraction and suspicion, and one of the key differences between the two is where the relationship lands at the ending. Although the heists are fun to watch in both versions, the real draw is the heat between Crown and the investigator, so I have to give this one to McQueen and Dunaway, who have great chemistry.
The Italian Job
– 1969 version (directed by Peter Collingson) / The Italian Job
– 2002 version (directed by F. Gary Gray)
The original gets an edge simply for having Michael Caine, but both of these are fast, exciting heist films. In the 1969 swinging Britannia version (also starring Noel Coward and wait for it…. Benny Hill), Caine goes for a heist in Italy involving a huge amount of gold and plans to prevent the cops from catching them during the getaway by causing an enormous traffic jam. It famously has an elaborate chase scene involving Mini Cooper cars. The American version starring Mark Wahlberg suffers in comparison mainly because he simply can’t compare to Michael Caine. But it is also stylish, although more slickly Hollywood with the Los Angeles setting and the addition of a revenge plot. Luckily it keeps the Mini Coopers! And the ending is extremely satisfying. These two movies are both for those times when you just want to watch something fun.
Ocean’s 11
– 1960 version (directed by Lewis Milestone) / Ocean’s Eleven 
– 2001 version (directed by Stephen Soderbergh)
This is one of those comparisons where it isn’t really close for me, as the Rat Pack version from 1960 is fun but not nearly as entertaining as the remake. And I love old movies, so I rarely prefer a remake! So let’s focus on the new one. Danny Ocean gets out of prison and immediately starts planning his next heist. He decides to pull together a crew and knock over not one but three Las Vegas casinos in one night. (In the 1960s version he gets his old army buddies to help and it’s five casinos). Much of the fun of the film is Danny, played by the suave George Clooney, assembling his team. He gets best friend Rusty (Brad Pitt) on board first, and they turn to old friend and former casino owner Rueben (Elliot Gould) to help plan the heist. The rest of the cast is equally fantastic, including Casey Affleck, Don Cheadle, Matt Damon and more. The heist itself is clever as hell and there’s even a love story to complicate their plans, when Danny’s ex-wife Tess (Julia Roberts) is involved with one of the casino owners. Although the original is fun as a cultural time capsule, the Soderbergh version is a real pleasure to watch, and is a great example of the genre. No wonder they keep making sequels!
Sneakers
(directed by Phil Alden Robinson)
Even though it is one of the less well-known movies on the list, this is one of my favorite movies. Like all good heist movies, it’s appeal lies in both it’s plot and it’s team of characters. While the plot is not showing it’s age, the characters are all still worth a revisit. Robert Redford stars as security expert Martin Bishop, who runs a team of hackers who help test companies for security vulnerabilities. Bishop is blackmailed by government agents who know about his illegal hacking past to take on a job stealing a mysterious black box. The heist is genius, but when they get the device they realize it is incredibly powerful, incredibly dangerous, and that they may have been pawns in a bigger game. This has high tension suspense, but also a lot of humor in the interplay between Bishop and his team. The dream cast includes Sidney Poitier, Dan Ackroyd, David Strathairn, River Phoenix, Mary McDonald and Ben Kingsley. Although the tech is a little dated now, it is still a hugely entertaining movie.
A Fish Called Wanda
(directed by Charles Crichton)
A heist/caper hybrid (my favorite kind!) in that there is a heist, but there’s also tons of humor and zaniness. It actually kicks off with the heist. A London gangster named George and his friend and animal lover Ken (Michael Palin) plan a jewel heist. They bring in American con artist Wanda (Jamie Lee Curtis) and Otto (Kevin Kline) a thug who thinks he’s an intellectual, to help pull the job. They get the diamonds, but are spotted driving away by an elderly woman. After stashing the jewels, Wanda and Otto turn in George to the cops, not realizing that he moved the jewels already. Wanda schemes to seduce George’s lawyer Archie (John Cleese) in order to get him to find out where the diamonds are now. It’s all craziness from start to finish, with that very British combination of wit and slapstick. Marvelous performances, especially from Curtis and Kline (who won an Oscar as Otto) make this one of the best heist comedies.
How to Steal a Million
(directed by William Wyler)
Oh my god, the style in this movie! It’s very 60s chic, with Audrey Hepburn dressed in one gorgeous Givenchy outfit after another. Audrey plays Nicole Bonnet, daughter of an art forger who poses as an art collector. When her father loans a forged statue to a museum, Nicole is sure he will get caught. Nicole recruits the help of suave society thief Simon Dermott (Peter O’Toole) to help steal the statue from the museum before they have a chance to authenticate it. The two have great chemistry, the banter is witty and the Paris setting is lovely. This is a light, airy caper that any fan of the genre should watch.
Out of Sight
(directed by Steven Soderbergh)
George Clooney plays Jack Foley, a bank robber in this stylish romantic heist film. As the film starts, Foley is breaking out of prison when he runs into U.S. Marshall Karen Sisco (Jennifer Lopez) and forces her to share the trunk of his getaway car. They are immediately sparky and attracted to each other, but they are on opposite sides of the law. Foley goes on to plan a big score with his best friend Buddy (Ving Rhames), robbing a man who was stupid enough to brag to them in prison about the diamonds he had in his house. But there is another crew of criminals after the jewels as well. Of course Foley and Sisco will meet again, and Soderbergh actually does a lot of fun things with non-linear storytelling. Based on a novel by Elmore Leonard, it’s no surprise that the dialogue sparkles. It didn’t do all that well in theaters, so if you missed this one, check it out!
Did I miss one of your favorites? Let me know!