A new Pynchon novel is always an event, and in the wake of Shadow Ticket‘s arrival in early October I’ve been reliving my own bookish past. I discovered Pynchon by reading V., Gravity’s Rainbow, and The Crying of Lot 49 in quick succession as a slightly extreme high schooler in the 1980s. I read through the stories in Slow Learner during college and wrote a long academic paper about Gravity’s Rainbow and Milton’s War in Heaven in Paradise Lost, but then somewhat missed the arrival of Vineland in February 1990, when I was traveling through Indonesia and Thailand in post-college vagabondage. Mason & Dixon in spring 1997 was a high-water event for my grad school novel reading community in New Haven. I lugged Against the Day everywhere with me on the London Tube in late 2006 when I was a fellow at the National Maritime Museum. Inherent Vice was a late-summer delight in August 2009, and Bleeding Edge slid into my fall 2013 Critical Theory class. I didn’t really expect another one from our eighty-eight year old reclusive author.
Shadow Ticket rounds out what we might call Pynchon’s Gumshoe Trilogy, as the third of a trio of late novels in which the main character is some kind of private investigator. Hicks McTaggart is less of a stoner than Doc Sportello in Inherent Vice and more of a heavy than Maxene Tarlow in Bleeding Edge, and in some ways Hicks’s conflicted past – his first job was as a head-banging strike-breaker – makes him even more morally compromised than Pynchon’s previous semi-outlaw PIs, Moral compromise, of course, has always been a key part of Pynchon’s paranoid and recursive world. The new novel provides a rousing portrait of the rise of fascism in the 1930s, from Milwaukee to Budapest, complete with an alt-history finish in which a millionaire’s coup replaces “that damned Bolshevik Roosevelt” (284) with General MacArthur. But even more than usual, I don’t think the plot was the main thing.

No one alive writes richer English sentences than Pynchon, even in his latter days. There’s a deepening, darkening rhythm, a falling-into something that briefly feels like order and insight but eventually slips into paranoia and uncertainty. Reading especially through the second, European half of the novel, I kept thinking about the contrast between frustrating narrative abundance and his gorgeous, serpentine, decadent sentences. Some of the best of these flourishing, turning gyroscopes open the book’s fairly short thirty-nine chapters. Here’s Daphne Airmont, searching central Europe for her lost clarinet-playing love, Hop Wingdale:
“For a while Daphne, flown into a dither, was chasing all over the map, trying to be there waiting wherever the puck might be on its way to but not always guessing right, along with wires going astray, trains running late, street-fighting and barricades to detour around and so forth, sleeping and eating when she can, usually within earshot of railway stations, steered along by tattered notices stuck onto public surfaces, helpful Swing Kids, Eukodal addicts with their own notions about the sequence and speed of passing events, Daphne continuing to run a train and a half, a day or a night or a street address behind, till eventually the charm wore off and she wound down to this pause in Budapest, where she figures to take a rest and wait to see if the band or any of its unknown fragments might find its way to her.” (Ch 26, p196)
The rhythm, the turnings, the ultimate lack of conclusion!
Or the next chapter, which sees our nostalgic Gumshoe wishing he could return to old Wisconsin –
“Sometimes all Hicks wants is to be back in Milwaukee, restored to normal life, to a country not yet gone Fascist, a place of clarity and safety, still snoozy and safe, brat smoke from a lunch wagon grill, some kid practicing accordion through an open window, first snow coming into town off the prairie, barroms where the smell of beer is generations deep, women in little round hats, Penny scales, newsstands run by war veterans named Sarge, everyday street doors that lead to nothing deeper than friendly speakeasies, El Productos in glass tubes, fried perch and coleslaw on Friday nights. Buttermilk crullers, goes witout saying.” (Ch 28, p210)
Of course we know that a not-yet Fascist America is a false dream – we’ve already been with Hicks to the Nazi bowling alley in Wisconsin, the coup is coming, and we also feels the contours of that other world, our world, in shadow, slipping down our own intermittently slow and fast ride into what sure feels, I hope not inexorably, like a Fascist future.
Maybe it’s that I’ve not yet taken the time to unravel fully the baroque plot-corners, but as I read Shadow Ticket for the first time, I was even less sure that usual that the coherence of the story was the main event. I don’t know that these two sentences are the best or most important sentences in the novel, but they strike me as prototypically Pynchon-ish, representations of the peculiar pleasures and complexities of this great American author.
Like many, I suspect, I’ve been mulling in recent weeks about how topical the old guy’s books feel in 2025, ever since Kathyrn Schulz observed in the New Yorker that “somewhere along the line our reality started to resemble, with uncanny specificity, the collected works of Thomas Pynchon.” I’ve been more than hip-deep in Pynchonia all fall, teaching The Crying of Lot 49 in my grad class, watching Paul Thomas Anderson’s semi-Pynchonisms spill out of “One Battle After Another,” and savoring the intermittent pleasures of Shadow Ticket slowly over the course of October. I even treated myself to all 55+ hours of the audiobook of Against the Day in September, and I tend to think that of all his novels, that’s the one closest to Shdadow Ticket in form and feeling. But now, as we emerge now into a new month, how much of the shadows will linger?
Thinking about the title of the novel makes me I’m also thinking about another old guy from Tom P.’s generation, who also released a late-career shadow in the 2020s. For Bob, it was the old guy’s 40th studio album, called “Shadow Kingdom: The Early Songs of Bob Dylan.” Bob and Tom have been, well, shadowing each other since long before Bob won the Nobel Prize that probably should have gone to Tom. Tom’s college buddy Richard Farina, who was married to Mimi Baez, sister of Joan, one of Bob’s most famous ex’s, was a folk-scene rival of sorts in the Greenwich Village ’60s, though in Richard’s case his motorcycle crash in 1966 killed him. Bob’s own 1966 motorcycle crash, the details of which remain murky, led to a period of isolation – do we know another great artist of this generation who hides from the press? What do these two old men have to do with each other? (For Tom’s shadow dissing of Bob, see David Hadju’s 2001 bio Positively Fourth Street: The Life and Times of Joan Baez, Bob Dylan, Mimi Baez Farina, and Richard Farina. I’m ready for Timmy C. in this movie!)
And I’m also wondering if Shadow Ticket will really be Old Tom’s signoff. If so, Hick’s youthful sidekick Skeet, who presumably will eventually become Zoyd Wheeler of Vineland‘s father, closes us out by lighting out for the territory on the Santa Fe Chief. “Right now we’ve got a couple of sunsets to chase” (293), Skeet concludes. A sentimental ending, somewhat like Mason & Dixon and Bleeding Edge? Not a bad way to close up shop, if the shop must close.
If the last three novels form one final trilogy, with Shadow Ticket’s Milwaukee poised halfway between Inherent Vice‘s California and Bleeding Edge‘s New York, perhaps these final lines suggest that our Eastern author, who presumably still lives on the Upper West Side, still longs for the West.
I think I’ll go back to Shadow Ticket soon. Or maybe it’s time for another whirl through Gravity’s Rainbow? Or Mason & Dixon?













