Issa Rae as Issa in HBO’s “Insecure.” (John P. Fleenor/HBO)

“Insecure,” the long-awaited HBO comedy from Issa Rae, premieres Sunday night. And it’s kind of a big deal.

Rae created the popular Web series “The Misadventures of Awkward Black Girl” and later penned a memoir of the same name. Rae starred as J, a self-proclaimed “awkward black girl” who struggled with everyday quandaries like how to interact with a co-worker approaching from the opposite end of a long hallway.

The series spun the mundane into hilarity, while defying stereotypes and effortlessly offering smart commentary on race and cultural perceptions. “Black people are always portrayed to be cool or overly dramatic,” Rae told The Washington Post in 2012. “Anything but awkward.”

Since the series became a cult hit in 2011, fans have wanted to see Rae make the transition from the Internet to prime time. She quickly caught the attention of networks including HBO and ABC, where she signed a deal to create a half-hour comedy through Shonda Rhimes’s production company, Shondaland. But the pilot wasn’t picked up. “I compromised my vision, and it didn’t end up the show that I wanted,” Rae told the New York Times last year. “It wasn’t funny anymore.”

In 2013, HBO circled back with Rae, who pitched what would become “Insecure.” She teamed up with veteran producer (and former “Nightly Show” host) Larry Wilmore to develop the show. Rae stars as Issa, a woman re-evaluating her career and less-than-motivated boyfriend as she enters the last year of her 20s. Her best friend, Molly (Yvonne Orji), is dealing with her own pre-30s angst — she’s a successful lawyer but is struggling in the dating world.

As noted by NPR, “Insecure” makes Rae the first black woman to create and star in her own premium cable show. “Isn’t it sad that it’s revolutionary?” Rae told NPR’s “Morning Edition.” “We don’t get to do that. We don’t get to just have a show about regular black people being basic.”

The first episode, which is available to stream now on HBO Go, begins with Issa fielding uncomfortable questions from middle-schoolers, accompanying Molly to an old-school nightclub and Facebook flirting with an ex.

It’s not “Awkward Black Girl,” but J and Issa do have several things in common, including a tendency to vent frustrations in the form of impromptu raps, usually performed in front of a bathroom mirror. In the “Insecure” pilot, Issa’s hobby randomly takes a bigger stage — to hilarious results.

Issa also navigates awkward situations at work — an unfortunately named nonprofit group (“We Got Ya’ll”), geared toward helping disadvantaged youth. She’s the only black person on staff and her co-workers are pretty tone-deaf when it comes to race.

Issa Rae as Issa and Yvonne Orji as Molly in HBO’s “Insecure.” (Anne Marie Fox/HBO)

But the heart of the show is really Issa’s friendship with Molly. A close friendship between two black women is a dynamic that isn’t seen often enough on television, and it feels especially poignant when the duo makes a fun reference to the long-running, revered UPN/CW show “Girlfriends” in the second episode.

As Rae finally makes her foray into television, she’s joined by another small-screen newcomer: Melina Matsoukas, who is known for directing masterful music videos, including Rihanna’s “We Found Love” (for which she won a Grammy) and Beyoncé’s showstopping “Formation.”

Matsoukas had never directed television before, but she was blown away by the pilot script. “I was just like, wow — my life on paper,” Matsoukas told Vanity Fair. “I totally relate to this girl and, you know, what she’s going through, being a black woman navigating through all these different spaces.”

Matsoukas isn’t the only Beyoncé collaborator to have a role on the show — the singer’s sister, Solange, who offers her own complex portrait of black womanhood in her newly released album, “A Seat At the Table,” is credited as a music consultant.

“Insecure” premieres Sunday at 10:30 on HBO. The first episode is available now on HBO Go.


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