A Funny Thing Happened on the Way to the Heist

Speaking of heists…

Once there was a goal-oriented criminal named Parker, a determined, friendless crook who let nothing and no one stop him. Parker was the sort of protagonist whom a hardworking author like Richard Stark (Donald E. Westlake writing under a pen name) could feature in book after book.

The Hot Rock would have been the thirteenth book in the Parker series…but the plot didn’t work as a Parker novel. The plot wanted to be funny. The deadly serious Parker was a poor fit for a comedic novel. A different protagonist was needed.

Thus was born one of the great characters of heist fiction: John Dortmunder. Career criminal. Master planner.

Possibly cursed?

Dortmunder has all the qualities and resources a successful criminal mastermind could need: intelligence, self-control, and a wide assortment of friends, each with their own area of expertise . The only thing keeping downtrodden Dortmunder from becoming New York’s Moriarty is his luck, which is consistently terrible. A straightforward commission to lift the Balabomo Emerald from a museum transforms into a series of increasingly audacious (and to the client’s alarm, increasingly expensive) crimes, none of which quite manage to deliver the titular rock into Dortmunder’s hands.

Just as Parker was the perfect lead for noir crime novels, hapless, likeable Dortmunder was the perfect lead for a comic heist series. There’s always stuff that needs stealing in New York; there are no end of unanticipated complications that can transform what was on paper a simple plan into a hilariously inconvenient maze of stumbling blocks for Dortmunder and his crew. It’s no surprise, therefore, that Westlake wrote fourteen novels and eleven or so short stories about John Dortmunder, Kelp, Murch, Tiny, and the rest of the crew before the author’s death put an end to the series.

The essential elements of a Dortmunder book are these: Dortmunder (sometimes against his better judgment) sets his eye on some valuable treasure. Having assessed the location and security of the coveted item, he composes a plan that can deal with all the known knowns and known unknowns. He then recruits fellow criminals with the necessary skills. Generally, his schemes go flawlessly up to this point. It’s only when he sets his plans in motion that things go horribly wrong, which they invariably do. Sometimes Dortmunder seriously wonders if he is cursed. But not seriously enough that he abandons his criminal career. Too bad for Dortmunder, hilarious for the reader.

***

  • The Hot Rock (1970)
    Dortmunder is hired to recover the Balabomo Emerald.
  • Bank Shot (1972)
    Dortmunder and crew scheme to steal—not rob—an entire bank.
  • Jimmy the Kid (1974)
    Dortmunder is convinced to use the plot from a (non-existent) Parker novel in an audacious kidnapping scheme.
  • Nobody’s Perfect (1977)
    Dortmunder is rescued from what might have been his third conviction and a life sentence. The only price? Carrying out what appears to be a straightforward art theft.
  • Why Me? (1983)
    What should have been an unremarkable jewel heist yields the Byzantine Fire, a superlatively valuable relic that numerous groups would be willing to murder to possess.
  • Good Behavior (1985)
    A narrow escape from the law leaves Dortmunder beholden to the one force he fears far more than the police: nuns who want him to do what they assure him is a simple little job.
  • Drowned Hopes (1990)
    Drafted to help his intimidating former cellmate retrieve a loot cache from the bottom of a reservoir, Dortmunder faces higher than normal stakes: if he fails to come up with a sufficiently ingenious method, his casually homicidal acquaintance will blow up the dam, killing thousands downstream.
  • Don’t Ask (1993)
    Dortmunder is hired to steal a holy femur, a relic which may determine which of two rival breakaway nations is admitted to the UN.
  • What’s the Worst That Could Happen? (1996)
    Dortmunder finds himself a theft victim when a smug billionaire, having caught Dortmunder in mid-crime, helps himself to Dortmunder’s lucky ring. Of course this means war….
  • Bad News (2001)
    Dortmunder ventures into new ground when he is hired for a bit of grave robbery.
  • The Road to Ruin (2004)
    Dortmunder’s cunning plan to gain access to a millionaire’s goods by infiltrating his household staff takes an unexpected turn when the boss is kidnapped. Loyal servant Dortmunder is taken along for the ride.…
  • Watch Your Back! (2005)
    A commission to loot the penthouse of one of New York’s most obnoxious oligarchs is complicated by Dortmunder’s dislike of his quite unlikeable client. Also, there are untoward developments at Dortmunder’s favourite bar.
  • What’s So Funny? (2007)
    Dortmunder is blackmailed by a crooked cop, who wants him to steal a valuable chessboard crafted for the Romanovs.
  • Get Real (2009)
    Dortmunder ventures into unlikely territory when he is convinced to perform one of his trademark capers on reality TV.

***

In addition to the novels, there were ten Dortmunder stories (plus a related take) in Thieves’ Dozen (2004), and a novella in Ed McBain’s anthology Transgressions (2005).

Many readers have opined that the best Dortmunder novel is Good Behavior, the one with the nuns. Me, I think the best was Drowned Hopes, which sets a non-violent Dortmunder against a former cellmate who is a lot like Parker. I enjoyed seeing my favourite Westlake character set against the man who inspired him.

If you’ve never read a Dortmunder book, give them a try even if your main jam is spec-fic. A master of prose, plot and character—a writer’s writer—Westlake is good enough to transcend genre preferences.

If you have read Dortmunder: what’s your favourite Dortmunder?

In the words of Wikipedia editor TexasAndroid, prolific book reviewer and perennial Darwin Award nominee James Davis Nicoll is of “questionable notability.” His work has appeared in Publishers Weekly and Romantic Times as well as on his own websites, James Nicoll Reviews and Young People Read Old SFF (where he is assisted by editor Karen Lofstrom and web person Adrienne L. Travis). He was a finalist for the 2019 Best Fan Writer Hugo Award, is one of four candidates for the 2020 Down Under Fan Fund, and is surprisingly flammable.

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