3. I, Libertine
In the 1950s, radio host Jean Shepherd was frustrated with the way bestseller lists were compiled, as not only sales of books for requests for books were taken into consideration. He organized a mass hoax by encouraging listeners to request the nonexistent book I, Libertine by Frederick R. Ewing at their local bookstores. This caused the novel to crawl up lists far enough, perpetuating its own buzz, for Ballantine to request the actual writing and publication of a book of that name. He enlisted science fiction authro Theodore Sturgeon to do so, and his point was proven. Here's a hilarious interview about it.
In 2004, a group of science fiction and fantasy authors were annoyed by vanity press PublishAmerica's claim to be a legit publisher that rejects most of the submitted manuscripts, as well as PublishAmerica's statement that, "the quality bar for sci-fi and fantasy is a lot lower than other fiction...[their authors] have no clue what it is to write real-life stories, and how to find them a home." They set out to write the worst possible piece of literary fiction imaginable, complete with two different chapters written from the same outline and with the same plot beats, a missing chapter 21, a chapter 17 that was word-for-word identical to chapter 4, two different chapter 12s, and one chapter spit out by a computer program that input the rest of the book and output semi-coherent sentences about the same characters. The characters, by the way, as well as being inconsistent in gender, race, age, and status of life (characters die and appear again without explanation), spell out with their initials, "PublishAmerica is a vanity press."
PublishAmerica accepted the book for publication. Zing.
In the late 1960s, a previous collective of 24 frustrated authors had written Naked Came the Stranger. But in this case, they were trying to make a point to the public in general instead of to a vanity press. Naked Came the Stranger was another an intentionally bad book, this one inspired by the fact that the bestseller list could be conquered only by books slathered in graphic eroticism. The collaboraters wrote an intentionally terrible book--often rewriting parts of it to make the language poorer--but put in tons of sex.
The book made it onto the New York Times bestseller list and spawned a film adaptation.