Poehler’s first months at S.N.L. were intense. In the aftermath of 9/11, there was an anthrax scare at NBC. Pundits speculated that there was no room for joking in a traumatized America. “No more fun. Good luck, everybody. Let’s hope that the building doesn’t explode!” was the mood, Poehler recalls. “It was so wild to be in New York then and have a new job that was so iconic,” one that involved finding ways to make the nation laugh. S.N.L. had a reputation as a boys’ club, but female performers and writers had suddenly achieved a critical mass, and some of the show’s most exciting material now revolved around women’s experiences. There were fake ads for Mom Jeans (“Give her something that says: I’m not a woman anymore; I’m a mom!”), Kotex Classic pads (“I love the belt; it’s so complicated,” Poehler exhorts), and Botox (“If someone told you all you had to do to get younger-looking skin was to inject a military-grade neurotoxin into your face every three weeks, wouldn’t you do it?” Rudolph asks soothingly).

Poehler says she always gravitated to Rudolph’s office, finding her intensely calm demeanor comforting in the middle of the high-wire act that is S.N.L. “So much of live performance is faking that you’re not scared,” Poehler says, “and Maya never seems scared—she always seems like she’s having fun.”

Rudolph looks pensive. “I do have a very, almost dead-calm demeanor. Almost a little too calm. But that’s not the show that’s playing on the inside.”

Their background in improv (Poehler at Chicago’s Second City alongside Fey and Dratch; Rudolph in the Groundlings, in L.A.) made them both good at creative collaboration, but Rudolph says that Poehler also has an instinct for gathering funny people together and creating an optimum atmosphere for them to play.

“Avengers assemble!” Poehler shouts. “I like the feeling of that.”

JUMP START

“When women are together, they’re really excited to be in their witchy circle,” Poehler says. Rudolph’s dress by Marc Jacobs; earrings by Jennifer Meyer; ring by J. Hannah; Handbags by Mark Cross. Poehler’s suit by Kate Spade; shirt by Tory Burch. Photograph by Art Streiber; Styled by Deborah Afshani. GOOD GRACIOUS

“I do have a very, almost dead-calm demeanor. Almost a little too calm. But that’s not the show that’s playing on the inside.” Dress by Marc Jacobs; earrings by Jennifer Meyer; ring by J. Hannah. Photograph by Art Streiber; Styled by Deborah Afshani.

The friendships forged on S.N.L. have not only endured but flourished creatively: Rudolph starred in Kristen Wiig’s Bridesmaids and Spivey’s TV series Up All Night, while Poehler and Fey headlined in Paula Pell’s Sisters. Their “sister wives” relationship (as Rudolph dubs it) only deepened with time; the demands of work and family meant that these women had to deliberately make the time to hang out. A few years ago, Poehler organized an IRL vacation, inviting Rudolph, Gasteyer, Pell, and Spivey to join her in a Napa Valley Airbnb for Dratch’s 50th birthday.

During the short flight there, Poehler went to the bathroom and, while pulling up her pants, became convinced she’d dropped her cell phone in the toilet. It was a devastating blow, since her phone held the obsessively detailed plans she’d made for the long weekend. Poehler found her friends’ reactions to her misfortune perfectly encapsulated their personalities. Rudolph instantly morphed into a maternal figure: “Let me get some gloves, I’m gonna look for that phone!” Spivey responded despairingly, according to Poehler: “This is my worst nightmare. If I lost my phone, I would die!” Pell offered to go with her to the Apple store as soon as they landed to buy a new one. Gasteyer shrugged off the panic: “Your phone’s in your bag. Don’t worry about it.”

Whatever the opposite of resting bitch face is, that’s what Poehler has—mischievous but never mean.

Poehler’s phone was in her bag.

A later jaunt to Palm Springs for Gasteyer’s 50th birthday, which they nicknamed “Muumuu Nitpick,” because everyone wore muumuus and bitched, was similarly jolly. Pell brought $800 worth of high-end vibrators as party favors. (She even packed batteries for everybody, because she is thoughtful that way.)

Poehler became convinced these trips were fodder for a film “not only because these are the greatest, funniest performers,” she says, “but there’s just not enough films that take full advantage of what it’s like to be our age and to be around women that have known you for a really long time but aren’t competing for the same job or the same guy.” Spivey and fellow S.N.L. vet Liz Cackowski wrote the screenplay for Wine Country; Poehler’s production company, Paper Kite, sold it to Netflix. They shot it over a seven-week period in Los Angeles and Napa. Gasteyer says her husband described the project to their kids as “the female version of The Hangover, set in wine country.” She prefers to think of it not as “a lost weekend so much as a found weekend.”