He is known for his constant in-joking and punning on the intersection between socialist ideologies and computer programming, as well as other fields. For example, his chapter titles such as "Trusted Third Parties" or "Revolutionary Platform" usually have double (or multiple) meanings. A future programmers union is called "Information Workers of the World Wide Web", or the Webblies, a reference to the Industrial Workers of the World, who are nicknamed the Wobblies. The Webblies idea formed a central part of the novel For the Win by Cory Doctorow and MacLeod is acknowledged as coining the term.[9] Doctorow and Charles Stross also used one of MacLeod's references to the singularity as "the rapture for nerds" as the title for their collaborative novel Rapture of the Nerds (although MacLeod denies coining the phrase[10]). There are also many references to, or puns on, zoology and palaeontology. For example, in The Stone Canal the title of the book, and many places described in it, are named after anatomical features of marine invertebrates such as starfish.
The Stone Canal (1996; US paperback ISBN0-8125-6864-8) – Prometheus Award winner, 1998; BSFA nominee, 1996[11]
The Cassini Division (1998; US paperback ISBN0-312-87044-2) – BSFA nominee, 1998;[12] Clarke, and Nebula Awards nominee, 1999[13]
The Sky Road (1999; US paperback ISBN0-8125-7759-0) BSFA Award winner, 1999;[13] Hugo Award nominee, 2001[14]– represents an 'alternate future' to the second two books, as its events diverge sharply due to a choice made differently by one of the protagonists in the middle of The Stone Canal[15]
This series is also available in two volumes:
Fractions: The First Half of the Fall Revolution (2009; US paperback ISBN0-7653-2068-1)
Divisions: The Second Half of the Fall Revolution (2009; US paperback ISBN0-7653-2119-X)
Engines of Light Trilogy
Cosmonaut Keep (2000; US paperback ISBN0-7653-4073-9) – Clarke Award nominee, 2001;[14] Hugo Award nominee, 2002[16] Begins the series with a first contact story in a speculative mid-21st century where a resurgently socialistUSSR (incorporating the European Union) is once again in opposition with the capitalist United States, then diverges into a story told on the other side of the galaxy of Earth-descended colonists trying to establish trade and relations within an interstellar empire of several species who travel from world to world at the speed of light.
The Restoration Game (2010). According to the author, "In The Restoration Game I revisited the fall of the Soviet Union, with a narrator who is at first a piece in a game played by others, and works her way up to becoming to some extent a player, but – as we see when we pull back at the end – is still part of a larger game."[24]
Intrusion (2012): "an Orwellian surveillance society installs sensors on pregnant women to prevent smoking or drinking; and these women also have to take a eugenic 'fix' to eliminate genetic anomalies.[24]
Descent (2014):[25] "My genre model for Descent was bloke-lit – that's basically first-person, self-serving, rueful confessional by a youngish man looking back on youthful stupidities... ... Descent is about flying saucers, hidden races, and Antonio Gramsci's concept of passive revolution, all set in a tale of Scottish middle class family life in and after the Great Depression of the 21st Century. Almost mainstream fiction, really."[24]
Short fiction
"The Web: Cydonia" (1998; UK paperback edition ISBN1-85881-640-8; part of the young adult fiction series The Web. Collected in Giant Lizards from Another Star)
"The Light Company" (1998) (quoting Ken MacLeod's blog: "The Light Company doesn't exist - the title was a provisional one, for purposes of a book contract, which I think got onto the publisher's list of forthcoming books and then took on a life of its own in the wild." - Ken, at Thursday, October 14, 2010 7:34:00 am)[26]
MacLeod, Ken (19 December 2012). "Never knowingly understated". The Early Days of A Better Nation. Retrieved 27 February 2014. Of the 27, I counted 15 who would give a definite Yes to independence. Only two of the others – Jenni Calder and myself – give a definite No.
Cory Doctorow (2010). For the Win. HarperVoyager. ISBN978-0765322166. MacLeod is thanked in the Acknowledgements section: "Many thanks to Ken MacLeod for letting me use IWWWW and 'Webbly.'"
"The Falling Rate of Profit, Red Hordes and Green Slime: What the Fall Revolution Books Are About"– Nova Express, Volume 6, Spring/Summer 2001, pp 19–21