According to legend, Bennington College is located in one of the few spots on Earth where all four winds meet, thereby imbuing the school with its overall haunted sizzle of alchemy. The twin forces of youth and genius, at least, were palpable in the air upon the arrival of the class of 1986, when three particular undergrads named Bret Easton Ellis, Donna Tartt, and Jonathan Lethem hit the campus, primed to flirt and flounder and follow their callings through their ensuing years at the decade’s most decadent college (which all three would later mythologize in their respective literary careers).
After first cracking open the school’s secret oral history for Esquire in 2019, Vanity Fair contributing editor Lili Anolik gives the Bennington Cinematic Universe the full podcast treatment via a new season of her Once Upon a Time… series. Together with Peabody–nominated C13Originals studios, Anolik sets the time machine back to the last great decade and chaperones a trip through the Gen X glory days in Vermont—as well as Oxford, Mississippi; Los Angeles; and New York—that turns campus mythology into dark academia canon.
The 14-part series premieres Wednesday; get an exclusive preview here:
Vanity Fair: Where did your fascination with the world of Bennington College in the ‘80s first begin?
Lili Anolik: I’ve been working on this story ever since I interviewed Bret Easton Ellis in the office of his West Hollywood condo about a movie he’d scripted, The Canyons, back in 2013. Sitting right there on his bookcase shelf was a hardcover copy of The Secret History, a novel I’d first read when I was 14, then reread probably once a year, every year, until I turned 25.
I remembered out loud that Donna Tartt had co-dedicated the book to him, and Bret said that he and Donna had been at Bennington together—then mentioned that they’d gone on a date freshman year. The date was, I’ll confess, a bit of a surprise since it was his boyfriend who, a few minutes before, had buzzed me up, but I rolled with it. I asked where they went that night, who paid, was there a kiss at the end, and I’ve asked him a million Bennington-related questions ever since. It was a casual conversation turned hardcore obsession.
Bret also mentioned that Jonathan Lethem had been in their class, too, and that Jonathan had written a piece about going to school with him and Donna. Donna, he said, had been angered by it. Of course, that stoked the flames of curiosity. Why was Donna pissed? I’ve often wondered if Bret, in that moment, could feel the power his words were working on my attention. He appears casual, maybe even a little checked out, but that’s just him playing possum. In any case, I felt that I had something wicked by the tail and I wasn’t about to let go.
For those who are totally unfamiliar with Bennington, how would you describe the “magic sauce” of that time and place that drew you in?
Art and transcendence, baby! Yes, Bret, Donna and Jonathan are major literary figures, but they’re also major cultural figures.
Bret, with American Psycho, predicted Donald Trump—name-checked in the novel 30 times!—as president of the United States. The roaring and adoring response Trump excites in the breast of Patrick Bateman foreshadowed what we saw happen with millions of MAGA supporters. Jonathan, with The Fortress of Solitude, which came out in 2003 and which traces the decades-long friendship of two Brooklyn kids—one white, one Black—was so ahead of its time as far as Black Lives Matter and racial reckonings go that it’s of our time.And Donna, with The Secret History, wrote the American Brideshead Revisited. She redefined the undergraduate experience. I certainly trotted off to college hoping to have my version of The Secret History.
And how would you describe the “magic sauce” behind this podcast?
Access. The podcast gives listeners access to worlds they probably officially disapprove of—so coke-y, so fuck-y, so entitled!—but secretly want to live in, or at least visit.
Bennington College, is the primary world, of course. You can, along with Bret Easton Ellis, steal the underpants of Quintana Roo Dunne, daughter of Joan Didion, after a night of debauchery. Or you can crash one of Donna Tartt’s alcoholic “tea parties,” held in her dorm room in Franklin House.
But there are also other worlds explored, too: The novel that made Bret famous, Less Than Zero, was written and published while he was at Bennington, but it’s based on experiences he had as a high school student at the Buckley School in Sherman Oaks. So, two early episodes of the podcast are devoted to the world of louche private-school Los Angeles, 1980-1982, a world of drugs and fame and fast cars and dead teenagers and the Billionaire Boys Club boys and girls who will grow up to be Desperate Housewives. Later, in the podcast, time will be spent in New York City café society, 1985-1989, where we’ll be keeping very fast, very famous company—Warhol and Basquiat; Molly Ringwald and Judd Nelson and Robert Downey Jr.; Jay McInerney and Michael J. Fox; Boy George and John Kennedy Jr. and certain members of Duran Duran.
What has the journey of reporting on these Bennington and adjacent circles been like?
It started as that piece for Esquire’s 2019 summer issue. And even in 2019, I’d been at the story for a long time, aggressively collecting Bennington voices. These voices were so wild and singular, so full of mania and intelligence, that I wanted to present them as au naturale as possible, which is why I wrote the Esquire piece as an oral history. But that still wasn’t enough. Yes, a voice says words and, yes, you can transcribe those words onto a page and, yes, a reader can glean some sense from them, but the words themselves only convey part of their meaning. The other part is conveyed in the delivery of those words—the spin the speaker puts on them. A podcast seemed like the right medium, and I’d loved working with C13Originals on my Traci Lords podcast, so the decision was pretty much a no-brainer.
As far as how the journey has gone for me personally—well, I’m still on it. I mean, I’m so deep inside this fantasy that I now live it. In June, I went for a walk along the Hudson River with Ian Gittler, the guy Bret showed his ‘suitcase full of drugs’ to first semester. Next week, I’m going for grilled cheese sandwiches with Madi Horstman, Jonathan Lethem’s Bennington girlfriend, the one who Sinead O’Connor apparently stole her bald look from—or so says Madi.
How hard was it to get the big three writers to talk—or not?
Bret is someone I now know pretty well. I see him with some regularity socially, and, when I do, I’m almost never not asking him about Bennington. But I interviewed him so extensively for the Esquire piece that I didn’t need to interview him anymore. I had something like 10 or 12 hours’ worth of tape.
Jonathan required a little persuading, though not much. He’s easy-going and just generally great. We stayed in touch over email after the Esquire piece. Because I’d drop by his office at Pomona College when I was in L.A., he opened up more in the additional interviews we did for the podcast.
Donna did not talk to me, neither for Esquire nor the podcast. I didn’t expect her to. She is perhaps the last private person in the social media age, and a self-mythologizer. She understands in a bone-deep way that rumor and innuendo grip the imagination far more powerfully than verified truth. Why on earth would she want to set the record straight with me? I did, however, get Donna’s characters and people in her orbit—friends, an ex-boyfriend, people who knew her when, et al.
That entire Donna half of the podcast is truly amazing; you’re basically giving us the origin story of The Secret History.
It should be catnip to the Dark Academia crowd. The Secret History is their Bible, their founding text, and I’m revealing the secret history of The Secret History. Like, I’m blabbing!
I think it’s important that I explicitly acknowledge here that The Secret History is not reportage, it’s literature. In other words, it’s an authentic work of art and magic. It can’t be decoded or demystified. So, the origin story of The Secret History that this podcast offers is really a way of getting closer to The Secret History or inside of The Secret History or just more of The Secret History. Closer to/inside of/more of The Secret History’s creator, Donna Tartt, as well, because her origin story is also told. I chronicle how Donna Tartt becomes “Donna Tartt,” this iconographically splendid creature with her sleek black bob, her beautifully tailored suits. To me, Donna Tartt is an American self-creation in the same way that Jay Gatsby is. She has that same aura of glamour and romance and fascination. And I don’t believe Gatsby’s aura was dimmed one bit by the revelation of his origin story, i.e., that he started life as Jimmy Gatz.
Finally, what do you think it is about this story and these central characters that make it all still so captivating to gossip about, almost four decades later?
Eve Babitz, I wrote about first for Vanity Fair, then later as a book, quoted—or, I guess, paraphrased—Virginia Woolf in her collection, Slow Days Fast Company: “Virginia Woolf said that people read fiction the same way they listen to gossip.” So, basically, gossip is the stuff of literature. Or it can be transformed into literature by an elevated sensibility. Bret, Donna and Jonathan certainly have that.
Once Upon a Time… at Bennington College is about gossip. But it’s also about art and America, literary and intellectual history, and the birth and evolution of creativity. And it’s about a place—Bennington in the 1980s, which was, in some ways, as fertile a ground for writers as North Beach in the 1950s or Haight-Ashbury in the 1960s. So, yes, this podcast is particular, but it’s universal, as well. In a sense, the whole culture went to Bennington.
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