It was 4 a.m. — well before New York City nightclubs closed in the 1920s — but Lois Long was on deadline. Reeking of highballs and still in her evening gown, she cabbed back down to the New Yorker offices on West 45th. There, reporters were still mashing their typewriters since the day before. She stumbled toward her office but stopped short. She’d forgotten the key.

The walls were short enough, she thought. She kicked off her shoes and dragged a chair over. Balancing on the doorknob, she managed to fold herself over the partition and crash to her desk, her unmentionables barely contained in her loose dress.

This was a common occurrence.

Lois Long was among the first staff writers hired at The New Yorker, where she both chronicled and lived the debauched, mostly inebriated life of a flapper — nearly every single night. Her exploits filled the pages of her column, written under the pseudonym “Lipstick.”

In fact, her exploits were so boozy and scandalous, they make Carrie Bradshaw’s two-martini lunch look like a child’s tea party.

Reporter Lois Long (right) gabbed with a New Yorker colleague in the early 1920s. (Wikimedia)

In the spring of 1925, The New Yorker’s founding editor, Harold Ross, needed money. And to get it he needed to juice newsstand sales. Launched the previous February, the publication was bleeding $8,000 per week. He was looking for smart, irreverent writers to weigh in on ”the week’s events in a manner not too serious,” with a voice “of gaiety, wit, and satire.”

So, he hired his “geniuses,” whom he called “Jesuses.” Among them, Long stood out. According to historian Joshua Zeitz, during her job interview, Ross asked her pointedly, “What can you do for this magazine?” She gave only a sly grin.

At that point, Long was working as a staff writer at Vanity Fair, and before that at Vogue. She came from academic stock in Stamford, Connecticut, and graduated from Vassar. But when Ross hired her at 23 years old, she would become the voice of New York City nightlife during the Roaring Twenties.

As described by longtime New Yorker contributor Brendan Gill, “She had plunged at once, joyously, into a New York that seemed always at play — a city of speakeasies, night clubs, tea dances, football weekends, and steamers sailing at midnight.”

Readers were enthralled by the illicit underground of back-door speakeasies, police raids, hooch dancers, and jazz luminaries. And Long knew all the passwords to the best clubs in town.

On a typical night, she and her friends might take a car to “21,” a famous speakeasy operated from a mansion on West 52nd Street. 21 managed to avoid closure by paying off police as well as registering as a “private club.” Still, the venue hid liquor behind a false brick wall that only opened by inserting a thin wire in precisely the right crevice. “Drinks were a dollar twenty-five,” Long wrote. “We thought brandy was the only safe thing to drink, because, we were told, a bootlegger couldn’t fake the smell and taste of cognac.”

After pre-gaming, the gang would spill up to Harlem, choosing among hundreds of speakeasies: The Spider’s Web, The Garden of Joy, The Drool Inn, The Bucket of Blood, The Yeah Man. “Above 125th Street, the latest place visited was the Club Harlem,” wrote Long. “Your first impression is of very pleasing decoration. The second impression is of a grand blues orchestra. And the third is probably the most inferior collection of white people you can see anywhere.”

After a night of music and lushing, Long and friends would “stumble home well after the stock exchange bell sounded the opening of business,” writes Zeitz.

Or they’d hit up The New Yorker bar for a nightcap. Ross had opened a speakeasy in the basement of nearby building in order to keep a better eye on his staff. Until one morning, managing editor Ralph Ingersoll came in and found Long and her future husband, New Yorker cartoonist Peter Arno, “stretched out on the sofa nude.” Admitted Long, “Arno and I may have been married to one another then; I can’t remember. Maybe we began drinking and forgot that we were married and had an apartment to go to.”

Ross closed the bar down.