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The Crying of Lot 49 is a 1966 novel by Thomas Pynchon. It is about a woman named Oedipa Maas who, in the process of acting as the executrix for her lover's estate, discovers among his possessions a set of bizarrely misprinted stamps. In trying to trace their origins and potential value, she accidentlly begins to unravel the rivalry between two medieval mail distribution companies, the Trystero and Thurn und Taxis -- a bitter and deadly rivalry that to her surprise appears to continue into the modern era. Or does it? She can't be sure she isn't just the subject of an elaborate prank being played upon her from beyond the grave by her late lover.

Despite being (or because it is) significantly shorter than the rest of Pynchon's novels (especially Against the Day and Mason & Dixon), it has become one of Pynchon's most popular books, after Gravity's Rainbow and possibly V.

Tropes used in The Crying of Lot 49 include:
  • Awesome McCoolname: Oedipa Maas, Dr. Hilarius, Genghis Cohen, Mike Fallopian, and a radio station called KCUF.
  • Bloody Hilarious: The Courier's Tragedy, a (fictional) Jacobean revenge play that is featured in Chapter 3.
  • Expy: Despite being from Southern California, the four members of the band The Paranoids are very similar to The Beatles. A nickname for The Beatles was "Los Paranoias."
  • Fun with Acronyms:
    • "Don't Ever Antagonize The Horn".
    • "We Await Silent Tristero's Empire".
  • Herr Doktor: Oedipa's psychiatrist reveals himself to be a former Nazi doctor who experimented on Jews.
  • Masquerade: If it's not all an elaborate prank, then the rival mail systems Tristero and Thurn und Taxis still exist in the modern day, hiding their existence -- and their bitter conflict -- from governments and society at large.
  • Milkman Conspiracy: W.A.S.T.E. Maybe.
  • Mind Screw: Like most (all?) of Pynchon's work, the story plays mind games not only with the reader but with the characters in it. In particular, Oedipa.
  • No Ending: Because it's a Pynchon novel.
  • Post Modernism
  • Shout-Out: When Serge of The Paranoids loses his eight-year old girlfriend to a middle-aged man, he writes a song that namechecks Humbert Humbert. As you would expect from a Pynchon novel, there are dozens of others.
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