In 2018—six years ago—on Thomas Pynchon’s 81st birthday, I put together a thoroughly unnecessary ranking of his eight novels. I’m somewhat ashamed of the post, as I included two novels I had abandoned a few times—Vineland and Bleeding Edge. Three years ago, on Pynchon’s 84th birthday, I wrote a few sentences on each of Pynchon’s novels, having, at that point, made my way through all of them. The first post, perhaps because it contains the word “ranking” in its title gets far more traffic to this day than the more thoughtful and finished post from 2021. Indeed, the “ranking” post regularly shows up in the top ten percentile of my weekly and monthly stats on Biblioklept, which, I guess, has bothered me enough to write this (thoroughly unnecessary still) “ranking.”
I know that if I were to approach Pynchon’s eight novels on eight different days, I’d likely end up with a consistent #1, #2, #3, and #8—but the other spots would shift depending on my memory or fancy or whatever spell I’d fallen under, chemical, metaphysical or otherwise. But here’s the list I came up with today.
8. Vineland (1990)
In my 2018 post (where I ranked Vineland at number 7) I noted that “Vineland seems to have a strange status for Pynchon cultists—its a cult novel in an oeuvre of cult novels,” and I’ve found that intuition confirmed over the years. I stick by my assertion in my 2021 post in which I asserted that “Vineland is ultimately depressing and easily my least-favorite Pynchon novel, but it does have some exquisite prose moments.” I’m sure I’ll revisit it before seeing Paul Thomas Anderson’s film adaptation though.
7. Inherent Vice (2009)
Speaking of Paul Thomas Anderson—I think I like his film adaptation of Inherent Vice more than I like the novel. And I love Inherent Vice. But I think PTA provides an emotional ballast that gives the narrative a center that’s missing from Pynchon’s novel (which is, likely, the point, or at least the byproduct of Pynchon’s shaggy dogging it). (I originally ranked Inherent Vice at number 6).
6. Bleeding Edge (2013)
So I finally found my way into Bleeding Edge in the earliest weeks of the COVID-19 lockdown. I’d stuck the book at the bottom of my 2018 list. I’m not really sure why I stalled out on—maybe it feels the closest to my own timeline of any Pynchon novel. Anyway, it’s one I want to revisit again soon. I riffed on it some in 2020, writing “Pynchon captures a time in America during which I was, at least theoretically, becoming an adult (a becoming which may or may not have happened yet). Reading Bleeding Edge helped evoke all the weirdness the 2000s were about to lay out for us. It made me angry again, or reminded me of the anger that I’d sustain for most of the decade. It reminded me of our huge ideological failure after 9/11, an ideological failure we are watching somehow fail even more today. But I also loved the novel’s unexpectedly sweet domestic plot, and found a kind of solace even in its affirmation of family, even as its final image pointed to the kind of radical inconclusiveness at the heart of being a parent.”
5. V. (1963)
So from here on out my rankings are identical to my stupid 2018 list, with that big caveat that I would easily swap, say, V. and 49 here. I’ll repeat my endorsement that “V. makes a good starting place for anyone new to Pynchon” and recommend that anyone interested in Pynchon but daunted by the scope check out the book from their library and read the ninth chapter, the story of of Kurt Mondaugen.
4. The Crying of Lot 49 (1966)
The Crying of Lot 49 is probably a better novel than V. but I think I like V. better. 49 is very funny and showcases Pynchon’s tonality of paranoia/hope wrapped up in zaniness/horror. It’s an excellent sophomore novel, but also dense, claustrophobic even. I guess I like the Pynchon sprawl a bit better.
3. Against the Day (2006)
Speaking of sprawl: Against the Day is Pynchon’s biggest novel, just fat and giddy and overstuffed with goodies. I think this novel would make an excellent American history textbook. Its thesis: resist the military-industrial-entertainment-complex. Start here!
2. Mason & Dixon (1997)
A measurement of the world and a story about friendship. It would be Pynchon’s best novel if he hadn’t written—
1. Gravity’s Rainbow (1973)
The best book. I reread it earlier this summer and it’s roomier and stranger and more rewarding each time.
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