Thomas Pynchon’s Novels Ranked Worst To Best

Thomas Pynchon is the post-modern master of our time and my favorite author. After finally finishing all of his books I decided to rank them in order from worst to best.

Slow Learner (1984)

Although released in the 80s, Slow Learner is a short story compliation, four of which were written before Pynchon’s debut novel. Unfortunately, none of the short stories are particularly interesting with Entropy as a possible exception. An avid Pynchon fan will find some value reading the stories and watching the evolution of his style, but from a purely literary perspective the collection does not offer much. The best thing about Slow Learner is the introduction where Pynchon gives his only attempt at an autobiography, cataloging his artistic progression and his life. That alone is worth picking up the book. It is oddly comforting to see a master of the craft talk about his struggles developing his technique, but I still have to place Slow Learner at the bottom of the list.

Mason & Dixon (1997)

Written seven years after Vineland, this novel saw Pynchon returning to his usual form of large-scale novels. Ostensibly it tells the story of Mason and Dixon, who charted out much of New England on the eve of the Revolutionary War. The novel is written in the style of an 18th century text, complete with odd spellings and punctuation. That presents a challenge right off the bat and can get a little tiresome after 800 pages of text. My biggest issue with Mason & Dixon is that it feels too gimmicky. Pynchon purposefully obscured the story with his gimmick of writing the book in old-style prose. It is an impressive feat, but does not lend well to an enjoyable reading experience. The novel has treasures, but overall is frustrating and even a little boring. It is only for Pynchon completionists.


V. (1963)

Pynchon’s debut novel is a twisting, kaleidoscopic tale spanning continents and decades. It is a miracle that the novel even works, let along as a debut novel. From the very start of his novelist career Pynchon took no prisoners, dropping readers into his fractured and fascinating world. V. presents significant challenges to first time readers. Following any central narrative through the seemingly unrelated stories is challenging, but sets up an important precedence for reading Pynchon: you just have to follow him through his world and let him unfold it at his own pace. Overall, V. is best read and understood in relation to Gravity’s Rainbow. Both books cover similar themes and even share some of the same characters. Gravity’s Rainbow just covers the territory better than V. does. As such, V. should be viewed as a prequel/sequel to Pynchon’s masterwork. It still stands on its own, but really shines in the spotlight of Gravity’s Rainbow.

The Crying of Lot 49 (1966)

At under 200 pages, The Crying of Lot 49 is generally recommended for people’s first exposure to Thomas Pynchon. It’s a good choice for starters. The short novel has all the great features of Pynchon’s books: loopy characters, conspiracy theories, intricate plots and kaleidoscopic pop culture references. However, it is also the most straight-forward book that Pynchon has written, with a clear plot that moves from point A to B. Pynchon himself hated the book, claiming that he had forgotten all the lessons he had learned from V. when he wrote it. As good as the novel is, you can see why he disliked it. There is nothing specifically unique about The Crying of Lot 49, but it does also give the most accessible introduction to classic Pynchon. Still, I can not rate it much higher.

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Inherent Vice (2009)

Inherent Vice is the funnest book that Pynchon ever wrote. Set at the end of the hippie era, Inherent Vice tells the story of Doc Sportello, a drug-addled private detective who gets caught up in a web of conspiracy and intrigue. Pynchon books have always been funny, but in Inherent Vice he really cuts loose, creating a loopy tale that reads the easiest out of all his novels. That is not to say that Inherent Vice does not offer challenges. The different conspiracies are purposefully obscured to give the reader a sense of experiencing them through the fog of marijuana. Once you realize that Pynchon is purposefully creating a drug haze through his prose, Inherent Vice becomes a joy to read. And while it is a fun novel, it is still poignant, cataloging the end of the hippie era with a deep sense of nostalgia and regret. It does not hit the same emotional highs as Vineland (which covers similar ideas), but is much more fun, and Doc Sportello is the best character that Pynchon has ever written.

Vineland (1990)

Taking a 17 year break after writing Gravity’s Rainbow, Pynchon returned with Vineland, which ended up being his biggest critical failure. At the time, Vineland was seen as a tremendous disappointment and many people still consider it Pynchon’s worst novel. Hindsight has been kinder to it though. When it came out, Vineland was disappointing because critics were expecting another Gravity’s Rainbow. But, in retrospect we can see that Vineland is more representative of the direction that Pynchon was going with his writing. In short, Vineland catalogs the death of the 60s and 70s counter-culture movement, especially as they became co-opted by the government and popular culture. Out of all Pynchon’s books, Vineland is the saddest. There is a palpable sense of nostalgia and regret throughout the text as Pynchon invites us to see how the unique counterculture of his young adulthood became nothing more than another capitalist product, regulating its participants to office workers and government employees. You get a sense that something tangible was lost in the 80s, something that the United States will never get back. It’s a depressing book, and one that needs rediscovery.


Bleeding Edge (2013)

While I love Vineland, this is the Pynchon novel that is the most criminally underrated. Bleeding Edge is his most recent work, released in 2013 and focusing on the way the September 11th attacks and the internet changed society. Straddling the line between Pynchon’s large novels like Gravity’s Rainbow and his shorter novels like Inherent Vice, this book is not extremely difficult to read, but does require a pretty good knowledge of late 90s/early 2000s popular culture. Bleeding Edge is most notable for its description of the Dark Web and its emotional recounting of September 11th. Pynchon never describes the attack in detail, but focuses on the effect it has on the characters, a dark nightmare just on the edges of their peripheral vision. Bleeding Edge is incredibly effective in creating a sense of anxiety and confusion that has characterized major changes in the 21st century, but overall ends on an optimistic note, a rarity for Pynchon.

Against The Day (2006)

Pynchon is always at his best when he is writing big, kaleidoscopic novels with tons of characters and plotlines. Nowhere is this more apparent than in Against The Day, the closest Pynchon has come to topping Gravity’s Rainbow. In short, Against The Day tells multiple intersecting stories about the world on the eve of World War I, starting at the 1893 Chicago World Fair and moving towards that cataclysmic war. At over 1,000 pages, Pynchon had tons of room to breath on Against The Day, stuffing it full of ideas and plot lines. However, unlike Mason & Dixon, this book is actually fun to read, and against all odds does not feel its length. After reading it, I felt like I had read multiple novels at once, each of which was expertly made. Keeping track of the plot lines is challenging, especially since some are direct mirrors of each other while others lead to dead ends. But there has never been and never will be a better book written about this time of history than Against The Day.


Gravity’s Rainbow (1973)

Was there any doubt that this would be on the top of my list? Not only is Gravity’s Rainbow Thomas Pynchon’s best book, it is also one of the best post-modern books ever, best post-war novel and possible the very best book ever written about World War II. But it is a beast. When I first read it I hated it. I skimmed through the last 100 pages, angry and resentful at Pynchon’s punishing prose. I was being dramatic, but the lesson stands: this is not a book for Pynchon beginners.

Ostensibly the story follows Tyrone Slothrop in his search through post-war Europe for the mystical V-2 rocket with serial number 00000. I use the adjective ostensibly, because Slothrop’s story only makes up a fraction of the book, but he is the closest thing in Gravity’s Rainbow to a main character. Throughout the 800 page novel, hundreds of characters slip in and out of the story, the narrative jumps to various time periods and locations, science mixes with poetry and in the end the reader is confronted with a manic, yet beautiful tapestry of ideas and stories.

Understand this: Gravity’s Rainbow is insane. It does not feel like the creation of a single human being. The sheer scale and scope of the story is staggering. Pynchon’s prose is at its best here, wildly careening between moments of slapstick, to serene beauty for lamentation on the lost innocence of our world, often times in the same section.

Describing exactly what Gravity’s Rainbow means is an impossible task, but the most common idea is the story of how our civilization came to love our own destruction. But that is just a chunk. It’s novel everybody should experience once (but preferably more than that).


3 responses to “Thomas Pynchon’s Novels Ranked Worst To Best

  1. Thank you for the applause-worthy effort that you went through in reading all of Pynchon’s works and ranking them with definite perspective. I will just disagree with you on both ‘Mason and Dixon’ and ‘The Crying Of Lot 49’. The former is intended as both an authentic epic and a farce of the same period in equal measure and once one gets past the deliberate language and the twisted humor of the conversations, one will enjoy it just like any other book. It is more heartfelt than most Pynchon stuff, I think. And ‘The Crying Of Lot’ was just perfect for its length, even as it was simpler it had all the hallmarks of classic Pynchon.

  2. Wow, you are quite prolific now. I guess marriage is agreeing with you. Keep up the good work! Love Gravity”s Rainbow. Need to read it again. I am getting to the age when I can read or watch something I have seen before and it’s like a brand new experience. I am really glad you are writing again.

    • Marriage has been going well for me. I’ve tried to establish a regular posting schedule of posting every Monday, Wednesday and Friday. I figure that if I want more people reading I should probably be more consistent with when I post.

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