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Once Upon a Time at Bennington College

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It’s the groves of academe: Bennington College, the wildest and wickedest school in America. In the last great decade: the 1980s. Bennington class of ’86, class of Bret Easton Ellis, future writer of American Psycho and co-leader of the literary Brat Pack; Jonathan Lethem, future writer of Motherless Brooklyn and MacArthur Fellow; and Donna Tartt, future writer of The Secret History and Pulitzer Prize winner. All three are, at various times, infatuated and disappointed with one another, their friendships stimulated and fueled by rivalry as much as affection. And all three will mythologize Bennington in their fiction—fiction that, as we’ll discover, isn’t always fiction, is often fact—and thereby become myths themselves.

From the Peabody-nominated C13Originals studios and Vanity Fair's Lili Anolik, comes the latest installment in the “Once Upon a Time…” franchise, Once Upon a Time… at Bennington College. This is a tale of money, murder, madness, and—of course—genius. This is, too, a multi-dimensional expose: the secret history of The Secret History revealed; the secret history of three of the greatest writers of Generation X revealed; and the secret history of Generation X itself revealed.

300 pages, Audiobook

Published September 29, 2021

7 people are currently reading
166 people want to read

About the author

Lili Anolik

8 books343 followers
Lili Anolik is a contributing editor at Vanity Fair. Her work has also appeared in Harper's, Esquire, and The Believer, among other publications. Her book, Hollywood's Eve: Eve Babitz and the Secret History of L.A., will be published by Scribner in January 2019.

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5 stars
36 (46%)
4 stars
24 (30%)
3 stars
10 (12%)
2 stars
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5 (6%)
Displaying 1 - 21 of 21 reviews
Profile Image for Megan.
381 reviews34 followers
January 6, 2022
The goss…it’s delicious.

Initially, due to the classic too-cliche fault of judging this podcast entirely by its cover, I refused to give it a listen. I barely skimmed the synopsis and somehow came to the conclusion that this was a fluffy piece role-playing Bret Easton Ellis and Donna Tartt, and couldn’t relax the sneer from my face.
This originated from a place where I couldn’t believe something this detailed, juicy and legitimately researched could actually exist when concerning my favourite ever-ellusive author.
when I finally clued in to the fact that the creator, Lili Anolik, was the journalist behind the Esquire piece on Bennington college, I immediately had to follow for the above reasons. (I also heard that Donna is attempting to sue Anolik for this podcast!! So obviously I needed to get in here! She should have known that would only make people more curious!)

Rather than a podcast, listening into the interviews and linking together the story of 3 of the greatest authors of the 80s - 90s, Once Upon a Time…at Bennington becomes a non-fiction audiobook that hypnotized me for days and cocooned me with a soft haze of drama, 80s decadence and debauchery (thanks to Bret), and a host of new-to-me authors to find and novels to read, that distracted from the terror of white-out road conditions and black-ice.

4/5 stars because as much as she tries to veer further into the lives of Bret Easton Ellis and Jonathan Lethem (the pod was a promised glimpse into the trio of literary award-winning, chart-topping Bennington peers that they make), their histories become overshadowed by the secret that is Donna Tartt (see what I did there).
Profile Image for lydia.
43 reviews
January 29, 2025
very well researched and informative and also scratched the itch I had after TSH. however there’s absolutely no way I could rate this five stars because it is SO invasive. jesus christ. no wonder Tartt tried to sue.

also I cared a lot less about the episodes surrounding Bret Easton Ellis and Jonathan Lethem but that’s just due to my general disinterest in them compared to Tartt lol
Profile Image for Mia.
441 reviews37 followers
September 9, 2022
i didn't know you could shelve podcasts on here, but this slapped. i've always wanted to learn more about bennington college and donna tartt's time there, so this really scratched an itch for me. i will say that at times it does feel like bret easton ellis and tartt are more characters in a drama than actual people, but such is the style of this podcast. overall, it was a really interesting piece of journalism.
Profile Image for Alex.
18 reviews
July 4, 2025
why is this on goodreads? anywayyy this shit is so trashy. i re-listen once a year :-/
Profile Image for Cori Diaz.
59 reviews2 followers
October 27, 2024
this was so brilliantly done and gave me the worst envy i’ve ever experienced. wdym 20-something writers in the 80s were throwing the best writer parties wdymmmm
Profile Image for Jason.
Author 23 books78 followers
December 14, 2021
I had no idea three of my favorite authors were classmates in the 80s at a small New England liberal arts college. I started reading Bret Easton Ellis in high school, discovered Donna Tartt's masterful The Secret History in college and gravitated to Jonathan Lethem sometime in my twenties or thirties. I've read all three are authors extensively, yet I was completely unaware of this convergence in their life stories until I listened to this a week at a time during my long commute to work in Northeast Ohio over a few months this fall. It's a great podcast, easily the equal of last year's Once Upon a Time in the Valley, which covered Traci Lords and the Southern California pornography industry. Lili Anolik has an excellent voice: part endearing wise-ass, part adult chatline operator and infinitely less grating than the twee cartoon characters inhabiting so many podcasts and public radio programs. Whip-smart and funny too. If she keeps making these, I'll keep listening, no matter what they're about. The story is great too, involving not only these three authors but also an assortment of friends and classmates and a surprising number of people who became famous in their own right: Brix Smith of The Fall (who played on most of the band's mid-80s masterpieces), actors Don Johnson and Nicolette Sheridan, many assorted major and minor figures from late-twentieth-century literature. At 14 episodes, the season runs a little longer (4 episodes longer, probably) than it needs to, but Anolik is certainly exhaustive in her research into these important writers and their orbits. Very enjoyable and well worth listening to.
Profile Image for Nayda.
6 reviews
December 23, 2025
This is the single most poorly structured piece of media I have ever come across. Anolik skips over all the most interesting parts (like Donna’s letters) in favor of summarizing them as quickly as possible and then inserting her own unnecessary interpretation and conjecture. Far too many tedious, irrelevant details and remarks and too few direct quotations and excerpts from interviews/letters. I don’t understand why everything is summarized and commentated on by Lily instead of just including more sizable clips of Matt Jacobson or Todd O’Neal speaking, since she managed to get interviews with them; this is such an incredible feat and any direct quotation from them is far more valuable than Anolik’s annoying interjections. The only people she does let speak are the ones who aren’t actually key players in the story, though those excerpts are choppy and overly commentated on, too.

I have a pretty passable existing knowledge about Bennington and the subjects of the podcast, yet I found it incredibly difficult to follow with all the subject changes and bizarre trajectory and structure Anolik chose to follow. Each time a topic got interesting she would include an entirely unnecessary and borderline unrelated parenthetical remark and then, for some inexplicable reason, change the topic entirely. It didn’t follow smoothly at all and I found it quite stressful. I don’t think Anolik is well suited for any kind of biographical work (as evidenced by Didion and Babitz, too) as she is unable to remain at all objective and maintain a streamlined, coherent narrative. She should pivot to auto-biographies, or think pieces, in my opinion.
7 reviews
October 19, 2025
I listened to this podcast the winter I worked in a winery where no customers ever visited. I was working on a sketchbook and listening to Lily Anolik piece together the days and nights that helped create some of my favorite fiction. This cast of characters who attended Bennington College, at the same time I was at the University of Washington, brought me back to those amazing times before mobile phones and the internet. It seemed so much easier to be creative and do cool things with friends that was all about reading, writing and discussions late into the evening. Cocktails and parties under the dark skies. This is what makes them so infamous. The Preppy Handbook Style combined with holding back a few secrets.

It helped that I knew these famous authors were living quiet lives. They were currently making art secluded in their homes, much the same way I was spending my time in my late 50's. Not one of us cared for fame (well, maybe Brett), they all felt they had something to say, to share, characters to create out of the Characters they knew in real life. They did it.
Time to start writing.
I recommend Season One: Once Upon a Time in the Valley. I listened to while reading Didion & Babitz. Iili has the career I would have loved had it been available to me in 1990.
Profile Image for Joschiko.
36 reviews
June 5, 2024
Rounded up 3.5 stars.

It's not hard to see why this podcast is problematic: Spreading rumours (even if based upon believable voices who knew the person of interest) about someone's sex life is not everyday dinner conversation. It's not just "X slept with Y" or "cheated on Y with Z" either. We're talking very intimate details that go into gender identity and sexual preferences "off the norm" (if you wanna use norms).

I also deducted half a star because Lili Anolik kind of annoyed me. She did a great job researching this but I feel like the whole thing could've been more compact and less blabla from her but that's just personal preference.

All in all, I liked it but feel guilty about that because I feel like I participated in something morally questionable as I'm pretty sure that Tartt wouldn't have agreed if someone asked her: "Yo, can I tell everyone that someone said you had a thing for posing as a boy and getting fucked up the ass?"
Profile Image for betty.
38 reviews1 follower
October 9, 2025
Loved listening to this so much I'm thinking about listening again as I make my way through these authors' body of work. Gossip = irresistible, lore = immaculate. I have drafted an entire list of brat pack books I want to go through someday just based on these random people that happened to be studying together at the same school. Ms Lili has a keen ear for scandal, which I admire (ideologically-speaking), and will definitely keep an eye on her. That Didion/Babitz book is calling to me... !!
Profile Image for Angie.
432 reviews
July 24, 2024
Lili Anolik kind of imposes herself too much in this story (a fact she acknowledges more than once, to be fair to her) but this was such a juicy listen. I’m gonna have to do more reading on Donna Tartt now because what I’m feeling right now about her isn’t particularly great tbh but she’s fascinating all the same.
Profile Image for taya.
10 reviews
March 6, 2025
it's entirely gossip, made for a crisp september evening with some hot bitter tea
Profile Image for Dylan.
Author 7 books16 followers
September 2, 2025
This is technically a podcast, but it might as well be an audiobook. My favorite podcast of all time as of now. Have listened to it fully twice, half of it a third time.
Profile Image for Sarah Greene.
38 reviews1 follower
January 17, 2022
This is elevated as it is delicious. Lili Anolik does the diligent down the wormhole work for you if you fall in love with the Secret History and passionately desire to know more about how it came into being. I loved hearing about the early days of Bret Easton Ellis and Donna Tartt and the origins of their American classics, Less than Zero and The Secret History. Lili Anolik distills and captures the most fascinating aspects of these literary heroes' personal stories.
Displaying 1 - 21 of 21 reviews

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