The Dortmunder Series
by Donald E. Westlake
Recommended Age: 14+
Okay, now I'm going to catch it, after telling you so many times how important it is to distinguish the bad guys from the good guys. But these are light-hearted books that will make you light-headed with laughter, so I don't think there's much harm.
Yes, Dortmunder is a cat burglar. He is, in fact, one of the greatest criminal masterminds ever to call New York City his home. He can dream up some of the most daring, impossible, and (all the same) fool-proof capers you can ask for, and carry them out - more or less - surrounded by his gang of humorous criminal associates. He trusts them too, as much as you can trust an honest crook. And he tries to restrain them from hurting people unnecessarily.
But Dortmunder is also a sad sack. And that's one of the things that makes these books so funny. Something or other is always getting him down. He wanders around with a put-upon expression, wincing at the amazing bad luck - and, when he needs bad luck, the unfortunate good luck - that always dogs his steps.
I first met Dortmunder in the book What's the Worst That Could Happen?, which was recently made into a movie that bore virtually no resemblance to the book. And I've been hooked on the crime fiction (most of it on the comical side) of Donald Westlake ever since. Several of his books have become movies, including the first Dortmunder novel, The Hot Rock. Other books in the series include Bad News, Don't Ask, Drowned Hopes, Good Behavior, Why Me, Nobody's Perfect, Jimmy the Kid, and Bank Shot.
I've been shopping in the young readers' section for so long, I'm not sure I can keep all of these books straight now, but I seem to remember that What's the Worst that Could Happen? involved a burglary that went so wrong that the owner of the house stole Dortmunder's "lucky" ring. Only I'm not sure it was such a lucky ring. Dortmunder goes on a spree, burgling all the homes owned by the same rich scoundrel, trying to get his ring back - and though he ends up with unexpectedly huge piles of loot, he grows increasingly discouraged by his "bad luck" at never managing to recapture the ring. It's a tale full of outrageous comedy, irony, and AMAZING criminal stunts that will, I guarantee, hook you on Dortmunder for the duration.
I also remember The Hot Rock quite well, since I've re-read it so many times. Aside from an in-joke for readers of The Pickwick Papers (look for the name of a law firm), it is outstanding for introducing the main characters in this long-running series, and forcing them to steal the same stupid piece of rock half a dozen times. Bad News is about a scam to horn in on an Indian casino's profits by robbing an Indian's grave, and Don't Ask is a hybrid of The Hot Rock and Bad News in which Dortmunder's crew has to keep stealing a certain bone that is of tremendous diplomatic value to a couple of ridiculous little third-world countries.
The titles of the many other comical crime books by Westlake (including those I haven't read) look just as entertaining, including The Spy in the Ointment and Trust Me on This. One that I have read is Smoke, about a vaguely Dortmunder-like cat burglar who finds himself turned invisible, against his will, and how he uses his newfound gift/curse for fun, profit, and revenge while some really nasty folks try to use him.
I can also personally recommend some of Westlake's chilling, "straight" novels, including The Ax and The Hook, which are NOT FOR THE FAINT AT HEART. The one is a bitterly ironic story about the lengths a man would go to in searching for a job (the thought being, your resume looks so much better if the more qualified candidates die suddenly). The other is about a macabre agreement between two professional writers, one of whom has trouble getting his books published, while the other is a blockbuster novelist with a serious case of writer's block. It's been years since I've read it, but to this day the thought of The Hook's ending still gives me the heebie-jeebies.
It all boils down to: this guy is a master of his craft. Whether he is trying to make you laugh or cringe, when you're reading one of his books, he's the one holding you in the palm of his hand. I'm going to keep looking for more of Westlake's books to add to my bookshelf. I hope you enjoy some of them too. EDIT: Currently on my "getting around to it" shelf is a Westlake crime novel titled Levine.