Vineland's Place in the Pynchon Canon
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Consider these three books:
*Crying of Lot 49 -- about the Sixties written in the Sixties.
*Vineland -- written in 1990 about the Reagan Eighties and the end of the Sixties Dream.
*Inherent Vice -- written in the 2000s about the Sixties.
I haven't read any of Late Pynchon: Mason & Dixon, Against the Day, and Inherent Vice So my analysis will focus on the early stuff I have read. It is interesting to note how the writer's latest book will re-contextualize every book he or she has written previously. After the labyrinthine genius of Gravity's Rainbow, Vineland does appear to be "weak beer."
Bolano and Pynchon appear similar in their creation of ramshackle, interconnected, ambitious works that reflect a strong authorial voice.
I totally understand your issues with Vineland Anything after Gravity's Rainbow can be considered a let-down, then again GR is a turgid carnival of brilliance. "Vineland" is also one of Pynchon's most personal and political novels. You definitely know where he stands on things.
Here's one of the long essays collected in the book, "Smoking Dope with Thomas Pynchon: A Sixties Memoir" by Andrew Gordon.