Issa Rae goes from ‘Awkward’ to ‘Insecure’ in new HBO comedy

The line between “Awkward” and “Insecure” has not been a straight one for Issa Rae.

The writer-actress struck a comic nerve in 2011 with “The Mis-Adventures of Awkward Black Girl,” her Web series about the often-embarrassing personal and professional woes of a single African American woman. Partly based on her life, the series, along with other projects on her YouTube channel, drew more than 25 million views and she adapted it into a bestselling book.

The L.A. native continues her misadventures with her new series, “Insecure,” premiering on HBO on Sunday.

Despite her massive fanbase and uniquely quirky viewpoint, Rae’s quest to jump from YouTube to TV has been bumpy.

Producers at various networks had trouble “getting her.” An ABC pilot crashed and burned, even with the support of powerhouse producer Shonda Rhimes (“Scandal”). And, until the last few months, shows from the points of views of people of color, particularly women, were not hot properties.

When she finally signed on with HBO and everything seemed to be falling into place, she lost her creative partner and showrunner Larry Wilmore, who left to do a late-night talk show at Comedy Central (which was recently canceled).

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When discussing HBO’s new series “Insecure,” writer-producer-actress Issa Rae says allowing viewers to ”watch black people be regular, to live their lives ... is an exciting thing for me.”

Rae has put those rough times in her rear-view mirror. Her dream is about to come true with Sunday’s premiere of “Insecure,” revolving around the friendship between two African American women dealing with their sometimes stormy relationship while also grappling with conflicts inside and outside black culture. Rae is the star, co-creator and executive producer, while her on-screen character — also named Issa — is once again uncomfortable and awkward, though more grounded than her Web persona.

“This is me,” Rae said of “Insecure” last week from her office in downtown Inglewood. “I identify as an awkward introvert. I have passive-aggressive tendencies. This show is more like me, more rooted in my personal experiences. In music terms, ‘Awkward Black Girl’ is the mixtape and ‘Insecure’ is the album.”

The realization of “Insecure” has made the memories of its evolution less painful for Rae.

“This has been a journey of ups and downs,” Rae said. “It’s been a test of my voice and my perseverance. Now, this is happening, and you forget all the years and the frustrations, everything that led up to this. You just say, ‘My gosh, this is finally happening,’ and now all I feel is anxiety, wanting people to see it.”

“Insecure” is debuting at a time when several shows from and about African Americans are landing in prime time. FX’s “Atlanta” from actor-comedian-rapper Donald Glover, MTV’s “Loosely Exactly Nicole” from comedian Nicole Byer and Netfilx’s “Luke Cage” have all premiered in the last month, receiving mostly positive responses from critics.

But Rae’s series has a clear distinction from the others: It is one of only two prime-time comedies in TV history created by and starring an African American woman. (The other was Fox’s short-lived “Wanda at Large” in 2003.)

Having that kind of historical significance is a bit of a double-edged sword for Rae. While she is grateful for the simultaneous presence of so many fresh voices, she is aware that her series may also come under more scrutiny.

“I do feel a light annoyance that some people will project all of black women’s experiences and woes on this show, and that’s not what I set out to do,” said Rae. “People may think I have to be the definitive voice. I just wanted to share a very specific experience and hope that people see themselves in these characters.”

She added, “Black women are varied and multi-faceted. Some won’t like this show, and some will identify with it, and that’s perfectly fine. That’s to be expected.”

In “Insecure,” Rae plays the sole black staffer of a community outreach organization based in South Los Angeles. She and best friend Molly (Yvonne Orji) are obviously close although they regularly clash. Her longtime boyfriend Lawrence (Jay Ellis) is having trouble getting on his feet after failing at a startup and is oblivious to Issa’s increasing doubts about their future

The series is a showcase for Rae’s infectious charisma and comic timing; her character often expresses her frustrations and inner thoughts while looking in the mirror. The dialogue is often raw and sexual and sprinkled frequently with the N-word.

Showrunner Prentice Penny sees “Insecure” as particularly topical in the current social climate where race has become a hotly debated national issue.

“This show is so important,” said Penny. “So much of our stories get reduced to our struggle and pain. There is not a lot out there about how we live on a Tuesday. This is black people just being people, showing our humanity.”

“Insecure,” with its predominantly black cast, also marks a milestone for HBO, which has come under fire in past years for its lack of diversity when it comes to lead characters on many of their most popular series, including “Sex and the City,” “Girls” and “Veep.”

The series is being paired with “Divorce,” a dark comedy starring Sarah Jessica Parker and Thomas Haden Church as a husband and wife at war with each other in an white upper-class suburban New York neighborhood.

HBO president of programming Casey Bloys compared Rae to other artists and HBO alum such as Larry David and the late Garry Shandling.

“The reason why they have been successful is because they are both writer and performer, and that comedic voice comes through clearer,” Bloys said. “What Issa is doing is being confident. She’s saying, ‘This is my version of being a black woman. It may not be your expectation or your voice, but it’s who I am.’ It’s honest. It’s great for us.”

Rae said she’s experienced some personal growth during the sometimes tortuous journey of the last several years.

“I’m more empathetic,” she said. “I’m getting more considerate. I’m more confident in my security. I’ve reached the end stage of where this character in the show is going.”

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Twitter:@GeBraxton