The Crying of Lot 49 (1965) - Yes!
V (1961) - No, but equivocally
Mason & Dixon (1997) - Yes!
Vineland (1990) - Yes
Inherent Vice (2009) - Yes
Against the Day (2006) - No
Bleeding Edge (2013) - Yes!
Slow Learner (1984) - Yes
This is my main assessment tool for books. I'm now in my 30s, so I've been wracking a little harder about it. Like there must be a way to finetune this instrument to be more predictive.
I'm glad I went through all of these. Some have that baseline style that really lifts Pynchon's floor. Even if you don't understand what all is going on, that's there to fall back on. I don't think all his books fall in the same place on the complexity scale. Inherent Vice wasn't complicated at all. The Crying of Lot 49 was pretty complicated. In fact thinking back on when I read it, I don't have a great feeling. I want to read it again; maybe I can get below a few more layers.
So that could be my next one. Or Bleeding Edge. That might be a safer bet. It appears less complex than COL49. Vineland makes a lot of sense on paper. PTA likely loves it (like he loves IV), so maybe it holds some similarity with that book as well. I'm not sure how labyrinthine Vineland is, so I'm cautious there. Mason & Dixon seems like an extraordinary commitment. The bit is great, but would I tire of it? I did read like 30 pages of it once before? I think that went well.
Those are the options. I can't read Inherent Vice again. It wouldn't be an awful time, but it'd feel performative or something to re-read it.
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