Start with The Hunter. It is barely two hundred pages, it was published in 1962 under the name Richard Stark, and it does one thing with total conviction: a man walks across a bridge into New York with nothing, having been shot and left for dead by his wife and his partner, and methodically takes his money back. There is no wit in it and almost no adjective. Reading it takes an afternoon and tells you immediately whether the harder half of Westlake's work is for you.
The obvious alternative is The hot rock, the first Dortmunder novel, and it is a perfectly good book — but it is a comedy built on the shape The Hunter established. The joke lands harder once you know the straight version. Read the Stark books first.
The Parker novels
Westlake wrote the Parker books as Richard Stark and kept the two identities genuinely separate for years. Our catalogue files them under his own name, which is tidier than the bookshelves in most shops, where they appear under both.
The Hunter (1962) comes first. The outfit (1963) is third in the sequence — the second, The Man with the Getaway Face, is not in our catalogue — and it is where the series widens from one grudge to an entire organisation. Parker robs the syndicate in a dozen cities at once, and Stark's flat procedural voice turns out to be very funny when applied to logistics.
Butcher's Moon (1974) is the capstone and should be read last of the three. It is the longest Parker novel, it brings back characters from most of the earlier books, and Stark wrote nothing more about Parker for twenty-three years afterwards. Reading it without the earlier volumes works, but you lose the roll call.
The Dortmunder comedies
The hot rock (1970) began as a Parker novel and turned into something else when the heist kept going wrong. Dortmunder is a competent professional in a universe that refuses to cooperate; the gang has to steal the same emerald five times. It is the funniest crime novel of its decade and the best entry to the comic half of the work.
Bank Shot (1972) follows directly, with the gang stealing an entire bank — the building, on wheels, while it operates from a mobile home. The premise sounds like it cannot sustain a novel. It does. Read these two in order; after them the Dortmunder books can be taken in any sequence, since the running jokes explain themselves.
The late standalone
The ax (1997) is the one to finish on, and it is not like anything else here. A downsized paper-industry executive works out that the way back to employment is to remove every rival for the one job he is qualified for. It is written in the first person, in the present tense, entirely without moralising, and it is the blackest thing Westlake published. Several readers find it unbearable. That is the intended effect.
Where to stop, and what is missing
There is no need to read all of Westlake — he published under at least a dozen names and the total runs past a hundred books. The Grofield spin-offs, the Cool and Lam-style comic capers written as Tucker Coe, and the late Parker revival novels are for people who have already decided. Five books do the job: The Hunter, The outfit, Butcher's Moon, The hot rock, The ax.
The full ordered path with per-stage notes is below.
Follow the full ordered path here: Donald Westlake books in order: where to start with Dortmunder and Parker.