Sam Bailey
Photo: Matthew Avignone

The night before she started shooting Brown Girls, a new web series she is directing, a nervous Sam Bailey threw up in her Humboldt Park apartment. Embarrassing, but less so than the afternoon in 2014 when, on the eve of filming her debut series, You’re So Talented, Bailey puked in front of a horde of commuters leaving the Red Line on Wells Street. “I didn’t use to do that,” the 28-year-old insists. “I guess I just care more now.”

Both incidents could be scenes in Brown Girls, which follows the misadventures of Chicago 20-somethings Leila (Nabila Hossain), who is Pakistani American, and Patricia (Sonia Denis), who is black. The show, penned by writer and poet Fatimah Asghar and premiering on Vimeo and Open TV on February 15, explores familiar themes: love (drunken run-ins with exes), sex (paying for a booty call’s Uber), and muddling one’s way through adulthood. But unlike so many shows about aimless young women, this one focuses exclusively on women of color. “These characters rarely get to exist on their own terms,” Bailey explains. “We fight, we mess up, we fuck stupid dudes. Just let us be normal, you know?”

Bailey’s work is a natural, if a bit weightier, descendant of web series like The Misadventures of Awkward Black Girl and Broad City, which propelled their creators (Issa Rae for Misadventures, Abbi Jacobson and Ilana Glazer for City) to TV development deals and mainstream acclaim. Both shows feature women getting themselves into (and out of) sticky situations, ground that Bailey mined for effect in You’re So Talented, which earned her a Gotham Award nomination in 2015.

Bailey’s ability to capture life’s messier moments is precisely what prompted Asghar to pursue her as a collaborator. “I love that Sam complicates things and lets her characters be mediocre,” says Asghar, who invited Bailey to read an early Brown Girls draft in 2016, hoping to pique her interest. “She never just accepts the clean narrative for how things are supposed to go.”

Bailey on the set of 'Brown Girls'
Bailey on the set of Brown Girls in August Photo: Greg Stephen Reigh

That comment also rings true for Bailey’s career. Raised in Logan Square, she began her stage training as a teen with Free Street Theater and Cross Town Ensemble and learned that she “loved the process of making things.”

After studying acting at Columbia College, she won small roles in several off-Loop productions. But Bailey quickly came to feel she was being cast primarily to add “diversity” and rarely in parts demanding nuance. “I had all these opinions about the work,” she says. “But nobody was asking for them.”

Her frustration peaked after she was cast in a role in which she was supposed to twerk while dressed as a slave and wielding a rifle. One night before rehearsal, she found herself sobbing as she memorized lines. “In hindsight, I shouldn’t have said yes,” she admits. “But for an actor, sometimes it feels like no isn’t an option.” Bailey left the production less than two weeks before opening night. Her departure caused a rift with the cast and director, but she felt liberated.

Soon after, she applied for a Second City Training Center fellowship for artists of color. Instead of auditioning with a scripted monologue, Bailey told a personal true story about an inappropriate relationship with a professor. The performance made an impression. “When she left the room, we were like, ‘Wow,’ ” artistic director Matt Hovde recalls. “She was clearly very open and knew exactly who she was.”

That confidence is on full display in Brown Girls. Bailey’s patient camera finds humor and pathos in long takes that highlight grounded and unvarnished performances. The result is more of the unfussy vibe that earned You’re So Talented shoutouts from BET, Bitch Media, and The A.V. Club.

Soon, Bailey hopes, a second season of Brown Girls will join a growing slate of projects. In December, she directed a Daryn Alexus music video that also featured pal Jamila Woods (who cowrote the theme song for Brown Girls), and this spring, she will shoot her first feature film, the story of a failed music label in 1960s Chicago. Wedged between: meetings with Hollywood agents who have taken notice. And while the siren call of Los Angeles may, in time, lure Bailey, her hometown will always have its appeal. “In Chicago,” she says, “we know how to make stuff.”


Web Series to Watch

Bailey dishes on her four favorites.

Kissing Walls

“Zak Payne, who created the show about the dating lives of young queer people of color in Chicago, captures embarrassment and awkwardness in a hilarious way.”


The Couple

“I’m a big fan of [co]creator Numa Perrier. This series is beautifully simple and nuanced. It inspired me to write You’re So Talented.”


Ackee & Saltfish

“It’s a love letter to two best friends who are black and British. There’s an episode about losing Lauryn Hill tickets that gets me every time.”



“Writer-director Amelia Umuhire really lets characters take up space and breathe. It’s a series that really takes its time—I’m into that.”