Born in Chicago in 1890, Keeler spent his childhood exclusively in this city, which was so beloved by the author that a large number of his works took place in and around it. In many of his novels, Keeler refers to Chicago as "the London of the west." The expression is explained in the opening of Thieves' Nights (1929):
"Here ... were seemingly the same hawkers ... selling the same goods ... here too was the confusion, the babble of tongues of many lands, the restless, shoving throng containing faces and features of a thousand racial castes, and last but not least, here on Halsted and Maxwell streets, Chicago, were the same dirt, flying bits of torn paper, and confusion that graced the junction of Middlesex and Whitechapel High streets far across the globe."
Other locales for Keeler novels include New Orleans and New York. In his later works, Keeler's settings are often more generic settings such as Big River, or a city in which all buildings and streets are either nameless or fictional. Keeler is known to have visited London at least once.
Keeler's mother was a widow several times over who operated a boarding house popular with theatrical performers. Beginning around age sixteen, Keeler wrote a steady stream of original short stories and serials that were subsequently published in many small pulp magazines of the day. He attended the Armour Institute (now the Illinois Institute of Technology), graduating with a degree in electrical engineering. When Keeler was about twenty, his mother committed him to an insane asylum for reasons unknown, thus fostering his interest in the insane, insane asylums and the sane who had been committed to such places, as well as a lifelong violent antipathy towards the psychiatric profession.
After graduation, he took a job as an electrician in a steel mill, working by day and writing by night. One of Keeler's early works was the science fiction story "John Jones' Dollar", about a dollar invested, which grows to a vast sum due to compound interest over thousands of years. It was at this time that Keeler met his future wife, Hazel Goodwin, whom he married in 1919.
Eight of Keeler's earliest works first appeared in pulp fiction magazines like Complete Novel and Top Notch.
His first four novels were originally released in England by Hutchinson, beginning in 1924, with The Voice of the Seven Sparrows. Beginning in 1927, E. P. Dutton took over publication of Keeler's novels in the US. Between 1927 and 1942, Dutton would go on to release 37 novels by Keeler. In the United Kingdom, publication of Keeler's novels, sometimes with altered titles and reworked prose, fell to Ward Lock who went on to publish 48 novels by Keeler from 1929 to 1953. The Voice of the Seven Sparrows introduced audiences the world over to Keeler's complicated "webwork" story lines with wildly improbable in-story coincidences and sometimes sheerly baffling conclusions. Keeler's complex, labyrinthine stories mostly alienated his intended reading audience.
Keeler's relations with the Duttons grew increasingly erratic and strained as his novels grew increasingly longer and correspondingly less and less popular. His 1941 novel The Peacock Fan appears to take a dig at the Duttons through a pair of faintly disguised characters, and in 1942 after releasing The Book with the Orange Leaves he was finally dropped by Dutton, although Ward Lock continued to issue his books in the United Kingdom until 1953.
Because of his initial popularity with Dutton, however, Keeler began to gain some notoriety in the mid-1930s as a purveyor of new and original stories. His popularity peaked when his book Sing Sing Nights was used to "suggest" two different low-budget mystery/adventure films, Sing Sing Nights (Monogram Pictures, 1933) and The Mysterious Mr. Wong (Monogram, 1935), the latter of which starred screen legend Bela Lugosi. During this period Keeler was employed as an editor for Ten Story Book, a popular pulp short-story magazine that also included photos of nude and scantily clad young women. Keeler proceeded to fill the spaces between the stories with his own peculiar brand of humor, as well as illustrations by his wife. (He also included frequent publicity for his own books.)
In his later career, Keeler's fiction and writing style grew increasingly bizarre, often substituting action or plot with laboriously lengthy dialogues and diatribes between characters. These events led his American publisher, Dutton, to drop him in 1942. The next eleven years were difficult for Keeler, as his writing drifted even further beyond the norm and short stories written by his wife (a moderately successful writer herself) were found increasingly within his novels. Keeler typically padded the length of his novels with the following device: his protagonist would find a magazine or book, would open it randomly and discover a story. At this point, Keeler's novel would stop dead in its tracks and he would insert the complete verbatim text of one of his wife's short stories, this being the story his novel's protagonist was reading. At the end of the story, the novel would continue where it left off, several pages nearer to its contractual minimum word count. These stories-within-the-novel typically contained only a few scraps of information that were relevant to the novel in which they appeared.
Keeler's novels were picked up by rental library publisher Phoenix Press, known in the business as the "last stop on the publishing bus." By 1953, British publishers Ward Lock & Co printed their final Keeler novel, thus forcing the writer to pen his stories exclusively for an overseas market with stories often translated for publication in Spain and Portugal.
Hazel died in 1960. Keeler, however, remarried in 1963 (to his onetime secretary Thelma Rinaldo), which rejuvenated his spirit for writing. Unfortunately, many of the new stories written by Keeler during this time went unpublished, including the relatively infamous The Scarlet Mummy. Keeler died in Chicago four years later, in 1967.
Most of Keeler's novels feature a "webwork plot." This can be defined as a plot that includes many strands or threads (each thread representing a character or significant object), which intersect in complex causal interactions. A webwork novel typically ends with a surprise revelation that clarifies these interactions retrospectively. According to Keeler's 1927 series of articles on plot theory, "The Mechanics (and Kinematics) of Web-Work Plot Construction," a webwork plot is typically built around a sequence in which the main character intersects at least four other strands, one after the other, and each of these encounters causes the next one. Keeler never claimed to have invented the webwork plot, but only to be its theorist and practitioner.
Keeler followed a writing procedure of his own; he'd often write a huge manuscript, perhaps twice the length required. He'd then cut it down to size, removing unnecessary subplots and incidents. The removed material (which he called "the Chunk") would sit around until Keeler wrote another manuscript to use it – which might result in yet another cutting procedure, and another "Chunk." In his book Thieves' Nights, the hero reads a book which is about two other men telling stories: a framing device within a framing device. In another book, Keeler and his wife turn up as characters in a story.
Keeler also kept a large file of newspaper clippings featuring unusual stories and incidents. He is reputed to have pasted these into the rough outlines of his novels, adding notes like "Have this happen to...."
Keeler is known for the MacGuffin-esque insertion of skulls into nearly all his stories. While many plots revolved around a skull or the use of one in a crime or ritual, others featured skulls merely as a side diversion, including one case where a human skull was used as a paperweight on the desk of a police detective.
Several of Keeler's novels make reference to a (fictitious) book titled The Way Out, which is apparently a tome of ancient Oriental wisdom. The significance of the nonexistent Way Out in Keeler's universe is equivalent to the role played by the Necronomicon within H. P. Lovecraft's Cthulhu Mythos.
Keeler has influenced science fiction writers such as Neil Gaiman and Futurama producer Ken Keeler (no relation); Ken Keeler says in the DVD commentary for "Time Keeps on Slippin'" that the story "Strange Romance" from the book Y. Cheung, Business Detective was an inspiration for the episode. In the late 1930s, British writer John Russell Fearn gave credit to Keeler for inspiring his experiments with webwork plots in his pulp SF stories.
Writer Jack Woodford wrote the article Tale Incredible: The True Story of Harry Stephen Keeler's Literary Rise about Keeler.
Keeler's webwork technique anticipates the so-called hysterical realism of later novelists such as Thomas Pynchon. Gabriele Rico in Writing the Natural Way advises aspiring writers to practice a form of webwork, which she calls "clustering", to encourage associational thinking which can be used to create characters and plot lines.
Films that exhibit probably unwitting similarities to Keeler's work include Murder Story (1989), in which Christopher Lee plays a Keeler-like character who keeps a large collection of newspaper clippings as part of his "Willard Hope Technique" for writing novels, which closely resembles Keeler's "webwork novel" technique. R. Kelly's series of music videos Trapped in the Closet shows a number of parallels to Keeler's style.
The independent studio United Film House is planning to release "The Flyer Hold-Up" in 2015. This film is based on a Keeler short story, The Flyer Hold Up; or, The Mystery of Train Thirty-Eight, published in the Chicago Ledger in four parts from December 4–25, 1915.
Tuddleton Trotter Series
The Mysterious Mr. I
Adventures of a Skull
The Big River Trilogy
The Way Out Series
Quiribus Brown Series
Hong Lei Chung Series
Ramble House Series