In the course of the last day I have been observing, and engaging with, an ongoing Twitter discussion (see: Dystopia2009 and MarkKohut) as to which Thomas Pynchon novel should be recommended to Pynchon newbies.
This might sound like a question of little import: just read the damn stuff. Indeed, this is the traditional advice offered by the Pynchon Wiki:
Don't believe what They tell you. Don't believe what you've heard, and here's what you've probably heard: Thomas Pynchon's novels are brilliant but difficult; the multiple plots twist and turn and rarely resolve; there are a gazillion characters; you'll need a dictionary and an encyclopedia to understand all the scientific metaphors and obscure words. This is the rap, and there is some truth to it. But it's not the whole truth, not nearly. As one seasoned reader of Pynchon put it, "difficult, schmifficult!"
To plunge down the rabbit hole of Pynchon's fiction is to commence a journey into another world, a world infused with magic and mystery, a wonderfully labyrinthine world where "real" history and fiction intersect and dissolve into dream. "Shall I project a world?" wonders Oedipa Maas, the heroine in Pynchon's second, and some say most accessible, novel, The Crying of Lot 49 (1966). Thomas Pynchon projects a world, and so does the reader. Onto Pynchon's richly detailed and often ambiguous landscape the reader projects his/her own interpretation in order to bring the work "into pulsing stelliferous Meaning" (Lot 49, p.82). This provides, as another long-time fan expressed it, "the tremendous pleasure bestowed on the reader of being in on a joint venture of a sort."
However, in spite of the faux modesty of this advice, Pynchon is a notoriously "difficult" writer. Gravity's Rainbow, for instance, has over 400 characters; the range of allusive historical and cultural reference can bewilder an unfamiliar reader; and his experimental literary style of character-shift and anachronic narrative temporality are confusing.
Leaving aside the question of "why" one should read Pynchon (I'll defer to the Pynchon Wiki here: the reward from these texts is phenomenal and they will haunt the reader for years to come), where should the curious reader start with Pynchon?
The traditional starting point, as partially echoed in the WikiHow article "How to read a Thomas Pynchon novel" and undergraduate courses worldwide, is to start with The Crying of Lot 49. This short and relatively accessible text acts as a mise-en-abîme for much of Pynchon's fiction, featuring, as it does: classical music played on the Kazoo, digressive asides, characters who accrue only a single mention before disappearing and an introduction to Pynchon's curious syntax. However, it by no means captures the awe-inspiring breadth of Gravity's Rainbow, which marks the highpoint (in my mind) of Pynchon's fiction.
Gravity's Rainbow, though, is sure to put off a good few people who might be tempted to plow through if they reap the rewards of Lot 49. Mark Kohut suggests that Pynchon's latest novel, Inherent Vice, could be a valuable starting place for its comedic tone and focus upon the era in which Pynchon wrote Gravity's Rainbow. This, again, is not unproblematic. There is a significant shift throughout Pynchon's career, marked in the turning point of Vineland and seen in Mason & Dixon, Against the Day and Inherent Vice towards what we might term, with thanks to Edward Said for the phrase, Pynchon's "late-style". This apparently self-conscious turn away from the odiously reductive label of metafiction towards the humanistic and more overtly political concerns of Pynchon's writing (which were, nonetheless, certainly present in V., Lot 49 and Gravity's Rainbow) is valuable in its own right.
However, yet again I feel that recommending anything post-Vineland as a starting point for someone interested in reading Pynchon will deprive them of the grandeur of the early work and, certainly with Against the Day, convince them that vast passages of Pynchon are tedious and overwritten. (Note: I am a big fan of Against the Day, but it took me several readings to appreciate it and I would not expect a newcomer to devote such effort to an author of which they were unsure.)
Verdict-wise, three different stances have emerged from this discussion.
Dystopia2009: I would not advise starting with AtD. I would now recommend either V. or CL49 to a new #Pynchon reader. #ThomasPynchon
As for myself, I would say the following: if you don't have time for Gravity's Rainbow, read The Crying of Lot 49. If you really want to know what it's all about, read GR.