Photography by Eric England
Curled up like a cat on a bar stool, mahogany hair falling in an Egyptian sphinx meets Beat poet cut, Chloe Stillwell could be any transplanted sophisticate on a Saturday night at the counter. The quiet din at Cafe Roze offers a lo-fi cloud of ennui or sangfroid, yet she appears in relaxed juxtaposition. Animated, well-modulated, leaning into a bevy of topics, she is the ultimate free spirit in a room of the well-put-together, self-conscious middle-agers.
Ahhh, the new Nashville, where the veneer is often deeper than the depths/content so many hipster-come-latelies embody. To look at the lithe young woman with the black clothes, the perfect batwing eyeliner, it’s hard to tell. Serious intellect? One more pretentious, poseur intellectual? Looks can be deceiving, or even more confusing, spot-on correct.
Chloe Stillwell, you see, has been nominated for a Pushcart Prize. For an essay. About her mother who had a stroke, who had 43 percent of her mental capabilities compromised, who sent her a Valentine. It is rich writing, dense with detail and a narrative sense of the emotions that had passed between them.
A Pushcart Prize, for those who don’t dangle over the literary abyss, is a big deal. Selected by the Pushcart Press to recognize the best work of small, independent presses, it celebrates “poetry, short stories, essays, memoirs, pieces of novels and what not.”
“Narratively does such amazing work, and to be one of six pieces (submitted) that represents them?” she says of the Pushcart honor. “I have a writing degree, a literary degree. You have to read every book from here to Genesis in that, and so there’s that. Writing feeds comedy, you know? But I think (the education) is what sets me apart. I write a set, but I’m a trained writer.”
This is the young feminist firebrand whose comedy tackles anal? Titty fucking? Waxing? This is the woman, with her small, fragile-seeming bones and ninja laser eyes, who almost created a local comedy meltdown by introducing a feminist comedy night at The 5 Spot? This is the instigator lobbing Molotov cocktails of sex and hypocrisy at the good ole boys doing the exact kind of humor you’d expect? The Pushcart Prize? Sure. Blow job jokes? Beneath her seeming intellect, and yet . . . scandalous when delivered by the person supposed to be giving, not mocking fellatio? Um, uh, yeah, guilty as charged.
Stillwell gets that joke, too. Even as she recoils in mock-horror over the stir the notion of a roomful of women comics getting real in the (pre)face of today’s “Me, Too” world, she mostly shrugs her shoulders. Comedy ain’t pretty, or dancing school.
Beyond her degree from Manhattan’s prestigious New School, the frequent Playboy contributor shakes her head and considers the double standard. “As someone who defends blue comedy, I so resent it. You know? When we did the night at The 5 Spot, a place that doesn’t do comedy as an established thing, there was a definite sense of being blacklisted. It’s passed now, but it was felt. People were telling me, ‘You’re too feminist and you’re too dirty.’ ”
And there was the night she finished her set, only to have the male host return to the stage with dismissive commentary, disguised as humor. “He’s calling me out with ‘Isn’t it just like the women’s lib girl to get up here and start talking about her pussy?’
“Why would he do that? A guy who does jokes about the vaginas of women in wheelchairs and fucking his girlfriend and driving at the same time?”
She has a point.
Chloe Stillwell, though, is hardly that simple. Born to a pair of traveling hotel singers, who settled down in Nashville when her mother was nine months pregnant, calling her childhood unorthodox would be like saying Alice in Wonderland is a weird story. It’s true, but you’re really just nicking the surface.
Stillwell & Holland, as her parents were known, had resort contracts all over America, playing in high-end hotels, singing a mix of contemporary hits and classics for tourists getting away from it all and businessmen killing time. Everything from Patsy Cline to Billy Joel populated the repertoire, and the pair — a “full-blooded, Oklahoma native, American Trail of Tears Cherokee” woman and a declared bisexual man — killed on the road.
Settling down, her father opened a recording studio, started a publishing company, and flourished on the creative side of life, while his wife began a work trajectory that saw her rise to CEO of an insurance company. These were people who had big personalities and were born to achieve; little Chloe didn’t fall far from the tree.
“I was never afraid to be the center of attention,” she says with an in-on-the-joke eye-roll. “I was always a funny kid, never in a theatrical way, but in a real-life way. I’d make my parents laugh, sometimes to break up the fights and bring the level down.”
Growing up on Love Circle, where Hillsboro Village served as her own little Greenwich Village, the tiny blonde flourished as an unusual child. She was enrolled in University School — “when I think of what my parents gave up so I could have that education” — and soaked up all the late nights, creative types, and processes she could find, watching the excess without realizing how excessive it was.
Everyone from Dobie Gray to Porter Wagoner put the child to bed on a cot in the studio’s basement, recognizing the hours were often too late for a little girl. The partying, though seemingly fun, didn’t appeal to
“I remember climbing up on a chair, then the counter, knowing there were hot chocolate packets above the microwave behind the whiskey bottles,” she says and laughs. “Taking those whiskey bottles down to get to the hot chocolate packets!”
Her determination to get what she needed set a pattern for life. With the classic “mean Mommy, fun Dad, which as a kid I took at face value” paradigm in place, Stillwell was also aware her mother’s drive — and demons — came from a deep place. “It was hard being on the reservation with a mom who was so incredibly abusive because she was mentally ill. She was so successful, because of that drive.
“She was super Virgo, super hardass, who had a brother die at 38. She was also, like a lot of Native Americans, allergic to alcohol; she’d hold her face differently after even just one drink.”
Add to that the real truth about her father. Though a declared bisexual, the man who saved her mother from the reservation really preferred men. “My dad was emotionally abusive (to her mother) because he was gay, and he wanted her to leave him. She loved to make scenes. Like any child, there’s just so much to all of it.”
Well, maybe not like any child. All families have dysfunction. But Stillwell’s family was a smelter that forged her comedic sense into something more focused, a tool to diffuse and distract. It also saw the acerbic kid land in rehab at 17 for cocaine addiction, while still making the kind of strong grades that earns admission to NYC’s prestigious New School.
That kind of formidable intellect can’t be stopped by a house of flamboyant people enjoying the party, and the after party, and the after-after party. At the New School, Stillwell aborted from the Parsons School’s photography/design curriculum — “I didn’t want to make art on a computer screen” — to the writing program on the advice of her University School advisor. There she worked with critic/cultural commentarist Margo Jefferson, poet and critic Albert Mobilio, film/music critic Charles Taylor, and historian/noted author Greil Marcus at the Eugene Lang College of Liberal Arts.
Moving from New York City to Los Angeles, Stillwell honed her writing chops, as well as studied comedy, with United Citizens Brigade (UCB). As a means of focusing on the way the unspoken uncomfortable yields large masses of hilarity, she found her apotheosis.
But Stillwell, appearing regularly in Narratively, Salon, Spin, Nerve, Mic, and Paste, felt the pull of home. Not entirely sure why, she found herself feeling the need to return to Nashville. Of the 2014 decision, she says, “I remember thinking, ‘You need to go back. You’ve been rambling. You got your degree.’ I wanted to start a life, to be closer to my family.”
She pauses. “I never intended to do comedy,” she continues. “I settled into freelancing, was spending time with my family and my boyfriend. And that’s when my mom had a massive stroke; wheelchair bound with cognitive challenges. I got to have that time with her before. I cherish it.”
It was a Valentine her mother painstakingly wrote out after it happened that inspired the Pushcart Prize-nominated essay for Narratively. Stillwell also found her writing for Playboy creating a wave; suddenly “Ed Sheeran Has a Toxic Masculinity Problem” was being discussed in the United Kingdom’s Guardian, as well as feminist blogs everywhere. “I got death threats over the Ed Sheeran,” she marvels. “I queefed that one out, never expected it to go viral. Who knew?”
But even realizing her education, her renewed family connection, the acclaim for — and response to — her writing, Stillwell felt something was missing. Though she didn’t think she wanted to be “a star,” the self-proclaimed introvert knew she
“Writing was going great, but it wasn’t satisfying that part of my life,” she explains. “The funny part — and the performing part. It takes a certain kind of writer to talk about dirty stuff, and make people laugh. I kinda did it to test my waters, to see how far can I go before someone says, ‘Whoa!’ But I realize anyone who’s not comfortable with dirty comedy, their trick is to shame it.”
Now aligning with Chicago’s nonprofit Women In Comedy, Stillwell recognizes the power comedy wields in terms of catharsis, as well as laughter. “The things we don’t talk about are hilarious,” she says. “People hear their fears, and things they’ve thought about privately — and (they) let the fears go when they start laughing.”
Raised on Jim Carey, Robin Williams, and Andy Kaufman, as well as female comics from Janeane Garofalo to Joan Rivers, the ability to dig in like a man reflects her influences. The notion of wearing makeup and looking pretty is an homage to Rivers, whom she declares, “the ultimate female comic.” Beyond those cornerstones, there are the original women of Saturday Night Live, especially Gilda Radnor “who mystified me how she held a camera while doing goofy stuff,” as well as the more contemporary Jen Kirkman, Eliza Schlesinger, Ali Wong, and Kristen Whig, who Stillwell calls “such an underrated comedy genius. Bridesmaids turned the tide; people went, ‘Oh! Women can be funny! They can write funny movies!’ ”
But even more than following in anyone’s footsteps — and don’t mention Amy Schumer, which earns the rancorous rebuke, “any woman doing dirty comedy gets compared to her” — Stillwell seeks to blaze her own trail. Discordant, real, borderline offensive, touching the raw spots in so many women’s psyches, it builds a base. But it has also help build a scene for comediennes in Nashville.
The Crying Wolf. Acme Feed. Zanies. But also, Memphis, Baltimore, New Orleans, D.C., New York City. They’re all places for Stillwell to stake her claim in 15-, 20-, 45-, 60-minute increments. Razing sacred cows, speaking the unthinkable, scalding the norms so many cling to, there is power in shocking, as well as dismantling people’s
“I like to write about pop culture in terms of contemporary reality,” she explains, drawing a line between published writing and her sets. “We’re talking about low-brow things from a high-brow point of view, mixing perspectives like this, things people don’t see coming, that’s where the impact is.”