With a government that bans books and censors public figures, and artificial intelligence that mimics writers’ voices and steals directly from their work, there are vanishingly few opportunities for writers to feel like “Masters of the Universe.” That is, except for a few blissful hours on Tuesday evening at the Waverly Inn, where Air Mail and Montblanc—the German pen-maker behind Wolfe’s favorite fountain pen, the Meisterstück—presented the first inaugural Tom Wolfe Prizes for Fiction & Reportage.

The Italian novelist Vincenzo Latronico, winner of the fiction prize for his millennial novel, Perfection, was the first to arrive. Hot on his heels and relieved that the nor’easter had subsided, a decidedly writerly crowd flooded in. Among them were Walter Isaacson, Jay McInerney, Amor Towles, Lisa Taddeo, Lili Anolik, and Meghan Daum, the other guest of honor, who won the prize for reportage for The Catastrophe Hour.

“This is a big surprise,” said Latronico, eyeing the turnout in disbelief while rolling his own cigarette. “I mean, the book was not successful in Italy. McNally Jackson alone sold more copies than the entirety of France.”

The more distinguished the crowd got, the more Latronico seemed to smoke. AIR MAIL Co-Editor Graydon Carter—a puff and a handshake. Seth Meyers, the master of ceremonies for the evening—another puff, followed by a quick lesson on how to pronounce his name. Bette Midler—two puffs. Matthew Broderick and Sarah Jessica Parker—a freshly rolled cigarette.

“Don’t you feel like we went back in a time machine? To, like, 1988?,” Parker asked Broderick in the center of the crowded room, where Alexandra Wolfe, Tom’s daughter, chatted with her mother, Sheila.

“Or 1947,” Broderick replied. “It’s like a writers’ salon.”

The actress Emma Roberts, who co-founded the online book club Belletrist and served on the committee for the Tom Wolfe Prizes, chatted nearby with her co-founder and fellow committee member, Karah Preiss. Authors Sloane Crosley and Emma Cline squeezed in between a gaggle of Spy alumni—Kurt Andersen, Aimée Bell, and David Kamp—while writers Dana Brown and Rich Cohen lingered by a cake in the shape of Wolfe’s signature white homburg hat, baked by Brooklyn chef Lauren Schofield. Bruce Wagner arrived with his partner, actress Jamie Rose, and screenwriter Scott Z. Burns came with Summer Sanchez-Cole. Also in attendance were Book of the Month C.E.O. John Lippman and McNally Jackson founder Sarah McNally.

Cocktail hour was a swarm, with everyone seeking out his drink of choice. “I’ll have anything but champagne!” shouted Isaacson to a waiter pressing a glass too close to his face. But after the guests were led from the garden to their seats in the main dining room, a sense of civility prevailed.

Following an introductory toast by Carter, Meyers praised Carter’s vision of a literary New York and said how such occasions were the stuff of dreams when he was growing up in New Hampshire. “I’ve always identified as a writer,” said Meyers. “I will never take for granted how special it is to be in a room like this one.”

The winners were announced by Alexandra Wolfe, who presented Latronico and Daum with 3D-printed statuettes that had been created from scans of her father’s actual homburg. Latronico and Daum spoke eloquently about everything from the importance of editors and translators to the impact of Tom Wolfe’s New Journalism on their work.

As the night went on, it became clear that there wasn’t a person in the room whom Wolfe hadn’t influenced, from writers such as The New York Times’s Shawn McCreesh and Alex Vadukul, Feed Me’s Emily Sundberg, and Vanity Fair’s Elise Taylor to editors such as Vanity Fair’s Mark Guiducci, The Spectator’s Orson Fry, and Aimée Bell of Simon & Schuster’s Gallery Books.

After dinner, guests collected gift bags filled with custom John Derian paperweights—featuring the work of master calligrapher Bernard Maisner—and Montblanc pens, and headed back into the garden for cake and more cocktails.

“This was one of those nights we will get to say we were there the first year,” Parker said on her way out.

Carolina de Armas is a Junior Editor at AIR MAIL