How ‘bossy gays’ made Ana Gasteyer a boss

By Chris Azzopardi

“This is what it feels like to be a superstar,” Ana Gasteyer remembers thinking the night she was at a New York City gay bar for a themed evening of Broadway sing-alongs. She doesn’t recall the exact bar or which of her “Saturday Night Live” characters its LGBTQ patrons were singing with en masse – maybe it was her animated impersonation of Celine Dion, maybe school music teacher Bobbi Mohan-Culp, she says – but Ana Gasteyer was there, dammit, fame welcoming her like never before: with a big, gay Broadway initiation.

It was 1996, the year Gasteyer became an “SNL” regular. With female co-stars Molly Shannon and Cheri Oteri, along with now-openly lesbian writer Paula Pell, the comedian was instrumental in disrupting the gender status quo on the late-night sketch show, which had long been male dominated. In those days, Gasteyer says she and her funny-lady cohorts were supported, naturally, by a devoted LGBTQ following.

“I do feel like gay men traditionally have had tremendous appreciation for women with a little more bite,” said the 52-year-old actress, “and they embrace female characterizations that cross a wider swath” than merely the dated female stereotypes some straight male filmmakers and directors fall back on.

Sometimes, however, films about women are best left to, you know, actual women. Gasteyer’s latest film, “Wine Country,” which premiered on Netflix in May, aligns with Hollywood’s current and belated shift in how women are characterized in film. They can be action heroes, and they can be best girlfriends who leave the hubby and kids at home so they can go on a mommy getaway and get messy. Directed by Amy Poehler, who stars alongside Gasteyer, Maya Rudolph, Rachel Dratch, Tina Fey, Emily Spivey and Paula Pell, the idea for the comedy originated after taking a real-life girls’ trip with her “SNL” friends to Napa Valley, California, for Dratch’s 50th birthday. Imagine the Golden Girls, but in a grassy field of grapes. Wine! Friendship! More wine!

“As people can come out more openly this is changing, but the gay community is like ground-zero for found family, for people who have to work to find their people and have to really nurture and embrace those relationships,” Gasteyer said. “I see it in a lot of gay friends; they have such deep loyalty to their crew, and “Wine Country” is about that: It’s about the support of your found family, about lifelong friends who may have a lot of differences and jagged edges at times but who are fundamentally there for each other in a way that is deeply unconditional.”

On numerous occasions during our interview, which took place in April in Napa on the rooftop of the Artesa Vineyards & Winery, a shooting location for the film, Gasteyer treads thoughtfully as to avoid generalizations she wishes not to make. She said, “I hate to stereotype…,” but safely assumes why “Wine Country” has spoken to at least “some” gay men who revere a strong woman: “It’s a bunch of fierce divas who are fantastic and connected and emotional.”

But it’s also as simple as, “Gay men have good taste and they know a good glass of wine.” (Her pro-tip, if you’re as intimidated as she is when in the presence of sophisticated wino gays: “Top-shelf Trader Joe’s; you can get yourself quite a deal.”)

They know a good, gay-friendly TV show, too. In 2016-2017, Gasteyer portrayed Karen Grisham on the queerish Netflix series “Lady Dynamite,” a role that cast her as the ruthless agent of the show’s main character, Maria Bamford (played by real-life comedian Maria Bamford, as a fictionalized version of herself). Grisham among them, the characters ran wild with their own eccentricities and offbeat energies – “and not just in terms of being women but just human beings,” she said.

I tell her that her projects always seem a little bit gay – and at this point we hadn’t even talked about her role as Elphaba in “Wicked” during its Chicago run in 2005-2006 and, a year later, on Broadway. But I have inadvertently underestimated the fundamental queerness of Ana Gasteyer’s work, and she laughs: “A little bit? It’s not really a coincidence.”

Gasteyer says it never dawned on her until this sit-down, but her relationship with the LGBTQ community began even before 1996, thanks to a gay friend who “sat me down.” He showed her videos of ’80s “SNL” cast members Nora Dunn and Jan Hooks, spurring her to break into the male-driven world of sketch comedy.

Her move to Los Angeles was the result of “another really bossy gay,” she said, laughing. “He was like, ‘You need to work in L.A.; you have a really distinctive voice, and I think you’re gonna work.’” Then, she went to one of the leading improv training programs in the country, The Groundlings, because “he told me to get my ass over to The Groundlings.”

“(He) just had a vision in a way that I didn’t for myself,” she adds.

During her six-season “SNL” run, from 1996 to 2002, Gasteyer was known for her absurdly spot-on impersonations of global gay icons Celine Dion and Martha Stewart; she also originated a slew of original characters including NPR’s “Delicious Dish” host Margaret Jo McCullin and Bobbi Mohan-Culp, half of the popular old-hat middle school music teachers with the perpetually “real hot mic” (Will Ferrell played her singing partner, Marty Culp). “They were such sort of earthy, crunchy, earnest, well-meaning nerds,” she says of the dowdy duo, laughing. For a 40th anniversary special of “SNL” that aired in 2015, Gasteyer joined Ferrell to reprise the Culps during a performance at an LGBTQ prom – exactly the kind of audience they would be singing for, she says: “In retrospect, we were often putting them in settings that were slightly underdog. It’s the kind of thing they would really root for anyway.”

You might say Gasteyer gravitates toward the underdog, as demonstrated by her part in “Mean Girls,” which imparted a special “too gay to function” kind of queerness into the greater cultural conversation. Released in 2004 – the film’s 15-year anniversary was in April – the queer-inclusive teen comedy featured Gasteyer as the overprotective mom, Betsy, of sheltered outsider Cady Heron (Lindsay Lohan). At the time, Gasteyer didn’t quite know the extent to which the film would resonate with LGBTQ audiences, but “it was right around the time of “Will & Grace,” when these things were just changing in the mass culture,” so she also wasn’t surprised that it did.

The Broadway adaptation of the film has introduced a new generation to its fetch story of female unity, including Gasteyer’s kids who she said are “deeply invested in it.” Recalling a recent exchange she had with her 11-year-old son, she erupts into a giddy laugh. Clad in a skull cap with a “Mean Girls” sweatshirt on, he said to Gasteyer, “Do I look too thug-y?” “I was like, ‘No. You’re wearing a Broadway musical sweatshirt. I think we’re clear.’”

Gasteyer, after all, knows a thing or two about musical-theater: Aside from her role as Elphaba, she starred in Fox’s 2017 live musical production of “The Christmas Story Live!,” portraying Mrs. Schwartz. Of course she can trill “My Heart Will Go On” for a laugh, but she also earnestly croons jazz numbers, as she did on her 2014 debut album, “I’m Hip.” Next, Gasteyer will release a collection of Christmas songs, including several comedic holiday tunes, called “Sugar & Booze,” out Oct. 25. Again, the songs are jazzy, which is good if you’re not big on jazz – because, no worries, Gasteyer will probably still be your friend. “We joke about it, but my husband and I have sort of a family thing that we tend to not be friends with people who don’t like food, animals or musicals,” she says, laughing, “and there are rules within that: Like, you’re allergic to dogs? Fine, whatever, I’ll forgive you.

“But I’m obviously a singer so I’m drawn to (musicals),” she continues, “and I think there’s something so naturally joyful and empathic about people who love musical-theater, because the function of really good music and a really good musical is that when the feelings get too big, you sing about them. So I think a gay audience, at least a traditional gay audience, is very dialed into their empathy.”

That, and wine. “Very” dialed into wine.

—As editor of Q Syndicate, the international LGBTQ wire service, Chris Azzopardi has interviewed a multitude of superstars, including Cher, Meryl Streep, Mariah Carey and Beyoncé. His work has also appeared in GQ, Vanity Fair and Billboard. Reach him via Twitter @chrisazzopardi.