At CrimeReads a list of ten novels about elaborate criminal plots. A few of those I've read (the films were really good, too):
...[I]mperturbably cool bank robber Jack Foley escapes from prison, but ends up locked in a trunk with Federal Marshal Karen Sisco. Leonard’s great ear for dialogue and deep sense of place and time give his books a unique feeling: the character-driven caper novel, in which, much like life, all our plans and plots confound and complicate each other in seemingly random ways. But like a pool hustler pulling off a sweet trick, all the balls ricochet off of each other and fall, elegantly, into perfect place.
Jim Thompson, The Getaway
Here the heist novel becomes a journey to the heart of noir darkness, as the classic pulp artist spins the tale of ace bank robber Doc McCoy and his wife Carol. Their path, from jail to job to a run for the border, is littered with double-crosses and betrayals, and ends in a symbolic hell where, inevitably, those who live by crime and deceit are doomed to devour each other. Also made into the awesome Steve McQueen/Ali McGraw movie by the equally great and grim Sam Peckinpah.
P.G. Wodehouse, The Code of the Woosters
A bit of a curveball, I know, or better yet a screwball, but farce shares a lot with the heist story: a plan is concocted to achieve some goal and immediately goes wrong, necessitating a new plan and so on, into glorious delirium. Bertie and his gentleman’s gentleman Jeeves are constantly conspiring to steal or retrieve treasured objects—in this case a coveted silver cow creamer—and their schemes involve all manner of disguises, impersonations, and climbing over walls and into windows while evading the cops, though the stakes, and the body count, are admittedly quite a bit lower. Read this as a refreshing break between the others, and meet the Maestro. There is no one better.
Jack Higgins, The Eagle Has Landed
I decided to end with this because it is both an interesting take on the form and exactly the kind of thrilling, suspenseful, high-spirited adventure that drew me to the caper book in the first place. Set during WWII, it concerns a German plot to, get this, kidnap Winston Churchill. The outlandishness of that scheme is only the beginning, but the intricate plan, the twists, crises, and daring solutions are expertly woven into real history—just the thing to capture the imagination of the fourteen-year-old in us all.
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