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(Duluoz Legend)

3.68  ·  Rating details ·  5,521 ratings  ·  295 reviews
Tristessa is the name with which Kerouac baptized Esperanza Villanueva, a Catholic Mexican young woman, a prostitute and addict to certain drugs, whom he fell in love with during one of his stays in Mexico -a country that he frequently visited - by the middle of the fifties. Wrapped in a spiritual atmosphere that expresses the yearnings of Kerouac to find himself, "Tristes ...more
Paperback, 96 pages
Published June 1st 1992 by Penguin Books (first published 1960)
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Average rating 3.68  · 
Rating details
 ·  5,521 ratings  ·  295 reviews

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Dave Schaafsma
Jul 07, 2013 rated it really liked it
Tristessa is one of Kerouac's supposedly "minor" books but unlike many others it is focused, short (at 96 pages) and is the story of Tristessa, a younger girl and junkie he loves (in a Buddhist way? tragically, unrequited?) from a distance, in Mexico, drunkenly. Has close observations of local scenes and her are vivid, desolate, and filled with "gone," romantic and lyrical detail.

Tristessa is, like so many of Kerouac's "lost" and "beat" heroines lovely, lost, inaccessible, romantic, tragic and
May 16, 2018 rated it really liked it
This is a novella of a story set in the mid-1950s Mexico City, where Jack has met a prostitute and drug addict named Tristessa (real name: Esperanza Villanueva), who he sees as either indigenous or a mestiza. She is the object of his love for a time: there's a year-long break in the middle, where it seems the events of "Dharma Bums" could've happened - and Jack makes a mistake of not declaring his feelings of love to her (view spoiler) ...more
Steven Godin
Jun 08, 2020 rated it really liked it
Shelves: america-canada
"Poor Tristessa is swaying there explaining all her
troubles, how she hasn't got enough money, she's
sick, she'll be sick in the morning and in the look
of her eye I caught perhaps the gesture of a shadow
of acceptance of the idea of me as a lover"

This a story about junk. And its one of the most truthful, painful, but at the same time saintly and beautiful pieces of writing I've come across by Kerouac so far. I've not always got on with his style, and would say its been embarrassingly sloppy in othe
Tristessa, you wily little book flighty as a cat, I should practice Satyagraha and resist my sinister urges to hoo haa your ever-loving Holy graces and wonder in the traces of your manna, all manna of manna, all eat-table and unbeatable and good and thirst-slaking, forsaking my faculties and reveling in the alacrity of all things, like you Mr. K., chronicler of the haloed hollowed hollow-cheeked hollerers of Holiness.

Kerouac, you sing-song like sacred ping-pong, rhythmically and hymnally and hip
robin friedman
Jun 13, 2014 rated it it was amazing

Many readers who love Kerouac consider "Tristessa" one of his finest novels. "Tristessa" has become the book of Kerouac that I return to most often. The book was initially rejected for publication, and it first appeared in paperback in 1960 following the success of "On the Road". The book initially may have been conceived as part of "On the Road." "Tristessa" is written in Kerouac's "spontaneous prose" style, with long rhythmic improvisational sentences and the feel of jazz. It is short
Jul 18, 2019 rated it really liked it
Shelves: jack-kerouac
[...] and the beauty of things must be that they end.
[...] humanbeings sow their own ground of trouble and stumble over the rocks of their own false erroring imagination, and life is hard.
[...] the fresh air of the night hits your newborn solitude...
Trouble is, what would I do with her once I’d won her?—it’s like winning an angel in hell and you are then entitled to go down with her to where it’s worse or maybe there’ll be light, some, down there, maybe it’s me’s crazy—
Matthew Ted
Better and more lyrical than the last Kerouac I read, his 'Satori in Paris'. A short novel about Kerouac in Mexico City, in love with a morphine addict called Tristessa. What a life he had. Some good, classic, Kerouac prose too. I have a library copy so I couldn't underline things so here's just one quote which I remembered from page 18.

'rosy golden angel of my days, and I can't touch her, wouldn't dare get up on a chair and trap in her corner and make her leery human teeth-grins trying to impre
George Ballin
Jan 20, 2018 rated it it was amazing
What to say about Tristessa? It´s a beautiful book but definately not for everyone. If you are ok with drugs, prostitution and despair this is a book for you. Needlessly to say I am.
Stuart Ayris
Oct 16, 2012 rated it it was amazing
Tristessa. What a beautiful name - you can't say it aloud wwithout feeling a sense of wonder, a sense of peace, a feeling that things are slowing down in the most perfect of ways. Yet this book (not sure it's a novel as it's not even a hundred pages yet not sure still it's a book as it's more like a film, a faded, dream sodden broken breaking film) is far from wonderous, far from peaceful and if pain is perfection then it's perfect indeed. Tristessa is what it's called and Tristessa is the name ...more
Evidence of a great talent in slow decline, but still a fun read nonetheless. Reminiscent of his shorter works such as The Scripture of the Golden Eternity as well as Mexico City Poems and Pomes All Sizes. Kerouac’s at his painterly best here, portraying both the horrors of opiate dependence and the despondency of life in a country without a strong economic base wholly without commentary. It is up to the reader to draw their own conclusions from this slim novella.

This book’s place within the “Du
Emily Seaman
I would actually rate this book a -1. Hated it. Read to page 20 TWICE (it's a 97 page book) and couldn't understand anything that was going on. Something about roosters. Call me crazy, but I require books with punctuation. ...more
Mar 03, 2015 rated it really liked it  ·  review of another edition
i never want to take morphine ever
Kevin Adams
May 22, 2021 rated it it was amazing  ·  review of another edition
Has always been one of my favorite Kerouac books. Short and well, I guess not sweet but you get what I’m saying. Underrated gem of his oeuvre, in my opinion.
Dec 17, 2012 rated it it was ok
Jack Kerouac is one of my all-time favorite writers, and a prime reason why I became a writer myself. The man wrote a slew of classic titles. However, Tristessa ain't one of them.

I feel like a heel for saying that, but it's only true. Tristessa is 96 pages of Jack Duluoz (Kerouac) mooning over a broken-down morphine junkie/whore who couldn't give a sh*t less about him. Kerouac compares this woman, who's based on a real-life fling he had down in Mexico City, to everyone from Ava Gardner and Grac
Aug 26, 2011 rated it really liked it
This is maybe a little more rambling/unstructured than usual for Kerouac (!), but overall, it's quintessential kerouacian stream-of-consciousness prose that's worth a read for when he finally hits his stride mid-book.

"since beginningless time and into the never-ending future, men have loved women without telling them, and the Lord has loved them without telling, and the void is not the void because there's nothing to be empty of."
May 18, 2016 rated it liked it
I myself can barely tolerate the writing of Kerouac. Too many run on sentences and drug addled thought processes. It's not that I absolutely hate it, but I think much of his popularity is based on name only without any regard to the finer details of his chaotic and exhausting prose. I feel as if I'm giving this a generous rating, based solely on the rare parts I actually happened to enjoy, while much of it was wasted effort to me. It was, and is, mainly an exercise of patience. ...more
Dec 13, 2012 rated it it was amazing
Tristessa was breath-takingly gorgeous! I realised half way through he'd just been sitting in a junkie's room in Mexico City (with Burroughs) and it had been fascinating! It was so beautifully written, and touching and sad and everything that I love best about Kerouac. ...more
Mindaugas Mozūras
Dec 23, 2019 rated it did not like it
Couldn't finish. The writing style of Jack Kerouac is not for me. ...more
Apr 07, 2010 rated it really liked it
Tristessa has always been a bit of an enigma for me. Some people claim that it's Kerouac at his best, others claim that it's a somewhat forgettable footnote to his career. Personally speaking, I found it to lie somewhere in the middle of those two takes, though I do find that it's a perfect example of Kerouac writing his daily life in a way that's just slightly more literary and beautiful than it probably was.

The first quarter or so of the book I thought fell a little short. I don't know what I
Joshua Nomen-Mutatio
Aug 21, 2008 rated it liked it
Recommends it for: my 15 year old self
My ratings for several books are based on how I felt about them when I read them. Several books that I loved/"really liked" I don't feel similarly about any longer, to put as simply and as fairly as possible. Kerouac is probably a perfect example of this. I loved reading about the melancholy psychological and geographical wanderings of Mr. Kerouac and his friends when I was 15 years old. It spoke to me in that way that people will describe books like On The Road and Catcher in the Rye as spe ...more
Frances Margaret
Sep 30, 2015 rated it it was amazing
Tristessa - the way it rolls down your tongue like a hiss, escaping like a slow death, is reminiscent of Kerouac's muse from Mexico. A long-time junky, dead eyes, dead love, dancing her way to ruins, untouchable.

One takes from this book the difficult but obvious truth, lessons greater than unrequited love. To fall in love with a junky is to step into a black hole. To live with a junky, one must become a junky. So all throughout this thing we have Jack tiptoeing around and against the void with h
Jesse Osborne
Feb 27, 2014 rated it really liked it
While it was morphine-addled and convoluted, all of it was breathtakingly beautiful. The way Tristessa loves everything, cares about nothing, wants so badly to understand but at the same time is addicted to not knowing. The way Jack worships her, her name becomes a deity, Tristessa. He loved her, but in the age-old "could never be with her" way. It was heartbreaking, a reflection of the impermanence of living/loving, the inevitability of loss, but also the effortless beauty of the "live fast, di ...more
Jan 02, 2013 rated it really liked it
The story has a power that just carries the reader along. I felt almost like the invisible companion of Kerouac shadowing him through the wet saturday night streets of Mexico city and into the lives of Tristessa and her companions. There are quite a few parts that I can't make any head or heel of but they for once - and it surprises me - they don't matter; they don't dampen anything that is beautiful about the stream of consciousness I was riding on. ...more
Jun 14, 2016 rated it it was ok
Just 96 pages. 96 pages usually just takes me an hour and a half to read, but this one took me days. This book was making my head spin. I need books with punctuation! Maybe Kerouac's head was spinning too (from all that morphine?) when he wrote this book. ...more
Nov 24, 2017 rated it it was ok
I realised I really don't like the stream of consciousness writing style after reading this. And Jack's (the name of both the protagonist and the author) drug-induced thoughts are incoherent and sometimes intelligible, that I don't even know what's going on half the time. ...more
Nov 28, 2018 rated it it was ok
the best part is his description of eating tacos in the rain
Aug 25, 2017 rated it really liked it  ·  review of another edition
Shelves: beat-generation
The ending is like a crescendo of rhyme and fast spitted words, and then it just ends. With no period. I could almost hear the music of it, like a jazz piano that tinkles along until it hits this brief, final note. Kerouac still intrigues me, particularly with the scenes where he's attempting to bond with the animals in contrast to how he's attempting to do the same with the junkies. I am beginning to find his character immature though, but I still enjoy the dare I say self indulgent way he cons ...more
Dan Leo
Jan 11, 2019 rated it really liked it
I recently had a bit of a Kerouac binge, and finally got around to "Tristessa" for the first time, which has about zero "story" in it, and, sure, a lot of it is gibberish, because it's classic "first and only draft" Kerouac spontaneous writing, probably fueled by bennies and pot, but it also has some great poetry in there. The sort of writing that is very easy to criticize and dismiss – its faults are all right there on the surface – but it has the value of originality and a sad broken beauty. I ...more
Sep 08, 2018 added it
Probably the first time I have ever read any book in one sitting. Second time through this one and it was even better than the first. Kerouac's prose is at his absolute peak here, my god. 100% perfect. ...more
Nov 28, 2019 rated it it was ok
In the first pages hardly understood what was going on. Dark and sad story.
And yes, I need books with punctuation.
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Jack Kerouac was born Jean-Louis Lebris de Kerouac on March 12, 1922, in Lowell, Massachusetts. Jack Kerouac's writing career began in the 1940s, but didn't meet with commercial success until 1957, when On the Road was published. The book became an American classic that defined the Beat Generation. Kerouac died on October 21, 1969, from an abdominal hemorrhage, at age 47.


Other books in the series

Duluoz Legend (1 - 10 of 14 books)
  • Atop an Underwood: Early Stories and Other Writings
  • Visions of Gerard
  • Dr. Sax
  • The Town and the City
  • Maggie Cassidy
  • Vanity of Duluoz: An Adventurous Education, 1935-46
  • On the Road
  • Visions of Cody
  • The Subterraneans
  • The Dharma Bums

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