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A Funny Thing Happened on the Way to the Heist

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A Funny Thing Happened on the Way to the Heist

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A Funny Thing Happened on the Way to the Heist

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Published on February 25, 2020

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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. Westlake1 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 expertise2 . 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.

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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 cursed3. 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 him4.

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.

[1]Westlake is best known for his mystery and crime novels, but he was also active in SF. Even after a famously intemperate flounce from Science Fiction (details here: https://www.existentialennui.com/2011/12/dont-call-us-well-call-you-donald-e.html), he penned a few speculative fiction novels, including 1992’s apocalyptic “Humans” and 1995’s “Smoke.”

[2]2: Parker is like Doc Savage; he has all the skills he needs to be self-sufficient. (Doc has a crew, but only because he likes pals who can congratulate him; he doesn’t need them to get stuff done.) Dortmunder is like Richard “The Avenger” Benson (https://en.wikipedia.org/wiki/Avenger_(pulp-magazine_character)), canny enough to know he is not omni-competent. He recruits people with the skills he does not have when he encounters them. The downside of Dortmunder’s approach is that each of his preferred partners in crime have in addition to their admitted skills a wide assortment of delightful quirks, few of which are entirely useful in a criminal context.

[3]Speaking of Dortmunder curses, despite the fact nothing about the books seems inherently unfilmable, not only have the movie adaptations been unsatisfactory, each has been worse than the previous one, miscast and sometimes rewritten for obscure reasons.

[4]Dortmunder versus Lawrence Block’s habitual burglar/involuntary sleuth Bernie Rhodenbarr would have also been a fun combination.

About the Author

James Davis Nicoll

Author

In the words of fanfiction author Musty181, current CSFFA Hall of Fame nominee, five-time Hugo finalist, prolific book reviewer, Beaverton contributor, and perennial Darwin Award nominee James Davis Nicoll “looks like a default mii with glasses.” His work has appeared in Interzone, Publishers Weekly and Romantic Times as well as on his own websites, 2025 Aurora Award finalist James Nicoll Reviews (where he is assisted by editor Karen Lofstrom and web person Adrienne L. Travis) and the 2021, 2022, 2023, and 2024 Aurora Award finalist Young People Read Old SFF (where he is assisted by web person Adrienne L. Travis). His Patreon can be found here.
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5 years ago

Re the movies: Jimmy the Kid was adapted for a Gary Coleman movie.
You might expect this would be the nadir of adaptations but nope. What’s the Worst That Could Happen was seemingly answered with “this movie.”

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5 years ago

I keep meaning to read more, but the climax of The Bank Shot is farcical perfection.

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5 years ago

Something about “Don’t Ask” in particular tickled my funny-bone (heh), but really, all these books are terrific.

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Gregory Morrow
5 years ago

Regarding footnote 4. Block and Westlake were good friends. At a signing once, I asked Block if he and Westlake had ever thought about a crossover. He answered yes, he’d even started an outline, but both realized that it would take a lot of work to make it work and they ultimately just weren’t that interested. IIRC.

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5 years ago

Bank Shot is probably my favorite. I admit I didn’t like Drowned Hopes as much because the homicidal character was just plain too evil.

I thought some of the later ones lost a bit of energy, but I read the entire series with great enjoyment. But I didn’t know about the short stories! Thanks — I’ll have to check them out.

My favorite parts, I think, were the planning sessions in the back room of the bar, and also the occasional clueless conversations of some of the patrons of the bar …

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5 years ago

And it’s strange — there have been some very good Parker adaptations, but as you say, the Dortmunder movies have been awful.

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5 years ago

Back when I was a first reader for the Mystery Guild, I was the one who got to handle the Westlake books. First book arrived in the form of a photocopied manuscript. It looked … odd … and it took me a while to spot why. It was clearly typed on a manual typewriter.

There were no typos.

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Russell H
5 years ago

Westlake also wrote an excellent article, “The Hardboiled Dicks,” on the origins and evolution of the “hardboiled detective” mystery subgenre, which is reprinted in the collection “The Getaway Car.”  Even if one is not interested in those stories or characters, it’s worth reading since Westlake shows how the genre has gone through cycles of what he calls “novelty” and  “ritual.”  That is, a writer will come up with an innovative “take” on genre that moves it in a new direction (“novelty’), that other writers will then follow, until that direction becomes a norm with standardized tropes and plot points (“ritual’), until another writer will come up with another new “take” (“novelty”, again).  The same template could be used to look at the origins and evolution of things like cyberpunk, steampunk, grimdark fantasy, etc.

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5 years ago

I just adore Dortmunder and crew! 😆

oldfan
5 years ago

The Bank Shot made my abdomen sore for days and my mother’s eyes roll so far she swore she saw her brain when I kept following her around reading bits to her.

Funny thing. She stopped buying them for me after that and the local library never ordered them.

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5 years ago

‘ Be on the lookout for a missing bank – ‘ I laughed myself sick too on that one.

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Divad
5 years ago

I don’t know if Westlake invented the phrase “Afghanistan Banana Stand”, as used in _The Hot Rock_, but that’s the oldest reference I’ve seen to it, and I’ve used it when needing a phrase unlikely to be said by accident.  It pops up now and then in other places, including a cross-time communication story in Analog.

oldfan
5 years ago

@7–There were no typos.

That…that’s impossible, surely! Inconceivable, and I *do* know what that word means, for someone who tried to learn to type on one of those beasts.

 

@11–To this good day.

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keiteag
5 years ago

I learned a lot from Westlake.  In another Westlake comic novel the main character recites the Jabberwocky to himself while waiting on hold on the phone.  I discovered you can use this to navigate phone menus.  Start reciting the Jabberwocky and you will almost immediately be connected to a real person.

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Keith Morrison
5 years ago

@6 …there have been some very good Parker adaptations, but as you say, the Dortmunder movies have been awful.

Parker is a simpler character to deal with; there’s been lots of films with a ruthless-yet-with-a-code villain protagonist in a serious crime drama, so filmmakers can fall back on well-known tropes that are accepted by audiences. There’s not a lot of complexity in making that sort of thing, and most people can agree on how it’s done, and because the main character is a criminal in their own right, anything questionable they do can be written off as, well, they’re a villain.

Comedy and farce, on the other hand, is very much more subjective and harder to do, and needs a lot more to go right, and then you’re still captive to audience opinion that can be very different from the filmmaker as to what they find funny.

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5 years ago

Jim Butcher, talking about SKIN GAME, said that every writer wants to write at least one heist novel.  That’s very true for all genres.  

Westlake is a funny writer.  I believe it was one of his novels where a long scene between two kidnap victims who are trying to talk with gags in their mouths is one of the funniest scenes I’ve ever read.  

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5 years ago

@7 and @12: I also read years ago that Rex Stout was able to type his Nero Wolfe stories, without typos, from start to finish.

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5 years ago

But shouldn’t a novel titled Don’t Ask come immediately *after* one titled What’s the Worst That Can Happen?

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5 years ago

@6 ecbatan: have to disagree with you there.  The Hot Rock is a wonderful movie!

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5 years ago

@1 tehanuw  I think The Hot Rock is a good movie, but it’s not a Dortmunder , since Redford is totally wrong for the character.

 

My favorite is probably Bank Shot or Good Behavior, but Drowned Hopes is close behind

BMcGovern
Admin
5 years ago

It’s funny–I really enjoyed The Hot Rock when I saw it years ago (I’ve had a thing for heist movies since I was a kid, and must have bounced from The Sting directly over to The Hot Rock at some point, without knowing it was based on a book for years). Then after James brought up these books ahead of this article last week, I picked up a copy of Good Behavior and inhaled it over the weekend…I really enjoyed it (smart, funny, and silly in just the right proportions), but I find I can only picture a mid-30s Robert Redford as Dortmunder in spite of the fact that he doesn’t fit Westlake’s descriptions at all. 

I guess I’ll have to read more of the novels until I get the right mental image. Or just learn to live with a Redford-y version of Dortmunder…(it’s really not so bad :)

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5 years ago

In 1990, my pick for Dortmunder might have been Fred Ward, but if I had to pick someone today it might be William H. Macy. Of course, since studios want star-power, who I would get is more likely to be Will Ferrell or Benedict Cumberbach….

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5 years ago

 @21 TV is funny that way. I read the Lovejoy books long after seeing the British show on A&E and was rather surprised, almost shocked, by how much the title character was “cleaned up” for TV.

OTOH, the Brother Cadfel show looked almost exactly like I imagined it would. 

6 of one, half a dozen of the other. 

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5 years ago

Ther’s a crossover in Drowned Hopes from Joe Gores’ 32 Cadillac, which is about a San Francisco detective agency out to repossess the titular cars. Two hilaroious books with the same scene, from two different angles.

Westlake was a genius, no question.

 

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Dan'l
5 years ago

One point that absolutely needs making — John Dortmunder and his crew are good at being bad. They aren’t incompetents, they just keep running into incredible streaks of bad luck.

The first two and Drowned Hopes are near perfection. (In fact, Westlake wrote one perfect caper book, but it wasn’t about Dortmunder. If you haven’t read Dancing Aztecs, run, don’t walk, to your favorite source for books and read it.)

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5 years ago

I wonder Kahawa has aged. It’s about the theft of an entire train off a single-track rail line.

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5 years ago

Good Behavior followed by Drowned Hopes are my favorite. I gave a copy of Drowned Hopes to a friend while they were in the hospital.  He said he initially had no clue why I would give a book like that to him (he was hard core SFF only as far as fiction went), but said he loved it.  I wound up getting copies of the whole series to that point for him.

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Martin
5 years ago

I’ve always thought a middle-aged Walter Matthau would have made a good Dortmunder.

I’ll join the chorus for Bank Shot as my favorite.  But they’re all good!

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Martin
5 years ago

A few of my favorite non-Dortmunder funny Westlake novels:

Trust Me on This and the sequel Baby, Would I Lie?  

High Adventure

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5 years ago

@29: And my first Westlake – “Dancing Aztecs”

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CHip
5 years ago

@7: wow. I’d guess erasable typing paper (a thing back when typewriters were common), but the ones I knew had an obvious tell: the surface was so shiny that copiers couldn’t get enough contrast, giving pale letters or a pale-gray background. Maybe he was just that good (or that fanatic about final drafts?).

Apparently I’m the only fan of What’s the Worst That Could Happen? In a way it’s both a perfect inversion of the usual Dortmunder heist (instead of money, his target is a bit of junk jewelry with purely sentimental value — but he keeps scoring larger and larger amounts of money while trying for this bit of trash) and a wrapup for the series, which makes the later ones a bit implausible (for the setup, not just the coincidences).

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David E. Siegel
5 years ago

I think Bank Shot was my favorite of the early Dortmunder novels, with perhaps The Road to Ruin my choice of the later ones, but Good Behavior is also wonderful, and each of them is at worst very good.  I would hate to have to choose only one.

I have long wondered how much Jimmy the Kid was meant to be an echo of “The Ransom of Red Chief”. It also includes perhaps 20% of the text of the otherwise unwritten Parker novel Child Heist, and “Richard Stark” appears briefly as a character.

I do not think that the violent anti-Dortmunder character of Drowned Hopes is actually much like Parker. Violence, particularly lethal violence is generally a last resort for Parker — not because he has a conscience, indeed he is a sympathetic sociopath — but because it tends to attract too much attention and is generally poor policy for a career criminal who wants to live to spend his money.

It should be noted that Parker’s luck is almost as consistently bad as Dortmunder’s. Either one of his associates will try to grab Parker’s share of the loot (generally a fatal error, for the grabber), or someone will see something at the wrong moment (Dirty Money), or someone else will try to horn in (for example The Split, The Green Eagle Score, or  The Jugger) or unpredictable unknowns will occur. The second and meatier half of most Parker books is how parker deals with the disaster, comming away with his skin, and sometimes the loot. 

It should also be notes that there is a cross-over between the Parker book Plunder Squad and  one of Joe Gores’s early DKA novels, I think it may have been Dead Skip, Dan Kearney, trying to track down a missing person, happens on to a group of crooks planning a heist — the leader is Parker. The scene appears in both books, and in each the VP character mentions the title of the other book. Much later, Parker makes an appearance in Cons, Scams & Grifts where it is said that the woman Parker holed up with on the run from jail shortly before the opening of The Hunter (The first Parker novel) was Kearney’s sister-in-lay, and Kearney met Parker then.

I always thought that the James Cann film Slither  could have had Dortmunder as the central characte with very little rewriting,

 

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Mike Schilling
4 years ago

It’s very unfair to Parker to say he’s like the treacherous, murderous Tom Jimson. Parker is loyal to his string (unless they betray him; then he kills without mercy), and doesn’t murder as a first resort.  Tom is, as his name suggests, not a Stark character but a Jim Thompson character. 

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3 years ago

First, thanks again James, I don’t know how I missed this article. 

I love this series, I like funny mixed in with….well…..everything😁. And for purely sentimental reasons The Hot Rock is my favorite. I saw the movie first, at a drive-in, parents would shove all the kids in one car and threaten bodily harm if we made trouble😂. I think it was the first movie I actually wanted to watch, asked my parents if I could sit with them. 

When I found out it was a book I was thrilled, and then more books with the crew and I was more thrilled. The only downside, like someone up thread said, is I picture all of them from the movie, not as they’re written😎

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3 years ago

My personal favorite is Bank Shot. You can’t beat ‘Be on the lookout for a missing bank…’

Another thing about Dortmunder’s crimes is while he’s not caught he never ever profits. He’s this brilliant mastermind who never makes any money off his crimes.