ISSA RAE TIMES TWO
The star of HBO’s ‘Insecure’ reflects on her real and her fictional selves
The moment seemed almost too perfect. Issa Rae, the stunningly talented and glammed-up star of her own HBO series, walking onto the stage at the BET Awards looking nothing like the “awkward black girl” who made her a YouTube star. But before she could reach the microphone, Rae was introduced as . . . Yara Shahidi.
No joke. Yara, of course, is 17 and plays Zoey on ABCs “Blackish.” Rae, 32, stars on HBO’s “Insecure,” which launches its second season Sunday.
“That’s Issa!” screamed Yvonne Orji, who plays Molly on “Insecure,” trying to correct the moment from her seat at the Microsoft Theatre.
Rae, after a pause and a stammer, pushed through a clumsy bit with host Leslie Jones to introduce a performance by SZA. Backstage, before returning to her seat, she texted her writing staff about what had happened and managed to retweet a spot-on analysis by a fan named Deon.
“Wouldn’t be @IssaRae if something awkward didn’t happen LOL,” Deon tweeted.
Deon’s right. For Rae, a creative dynamo capable of turning heads on the red carpet and in the writing room, these moments just happen, whether in real life or on a set. And Rae’s ability to turn everything, whether a disastrous date or a workplace bumble, into comedy has carried her from You-
sensation to a different kind of leading lady. In “Insecure,” she plays Issa Dee, who can show viewers her vulnerability without totally showing her hand, a character as self-assured as she is self-loathing. She’s funny, maddening, manipulative and trying her best. To her legion of fans, she’s simply Issa.
Which, interestingly enough, is something the real Issa admits has started to get tiresome. As Rae grows older, she’s finding it less charming to be confused with this fictitious Issa. If only she had named her “Insecure” character Nia or Amani.
“I just didn’t think. I was so pressed with telling a good story that I didn’t think about the fact that this character, named after me, was going to air,” Rae said last month on her way to the BET Awards. “And even while shooting, it didn’t cross my mind until it aired. This is not by any means my life, and this is where it gets muddy because people assume that it is.”
Or, as “Insecure” writer Laura Kittrell puts it, “People think they know Issa in a way that’s different than the leads of most shows. I don’t think people are necessarily walking up to Sarah Jessica Parker and saying, ‘Oh, she’s Carrie Bradshaw.’ ”
More than six years have passed since Rae emerged on YouTube as the creator and star of “The Mis-Adventures of Awkward Black Girl.” The Web series, clicked on by millions of viewers, led to a false start (a failed pilot for ABC), a chatty, unvarnished memoir and, finally, “Insecure,” which she developed with veteran comedian and writer Larry Wilmore.
The show’s acclaimed first season packed much of what’s driven classic sitcoms — office conflict, dating foibles, dishy friends — with much that is rarely, if ever, seen on TV. The show’s blackness is as essential as its comic sensibility. And because they’re intertwined, “Insecure” can pull off hilarious, twisting subplots, such as season one’s unforgettable “broken p---y” debacle, a drunken rap turned into a girl-feud turned into a social media disaster. “Insecure” also puts a spin on how race plays out in the workplace with a specificity never before seen on a sitcom. “Insecure” producer Prentice Penny describes this as capturing the “paper cuts of racism.”
“Where the white co-workers are sending each other emails about the uncertainty of Issa planning the beach day, or the boss asking Molly to talk to the black co-worker,” he says. “Things like that where it doesn’t come off as so in your face.”
Director Ava DuVernay, whose own TV drama, “Queen Sugar,” recently kicked off its second season, is just glad “Insecure” exists. She has never bought into the criticism of “Girls” creator Lena Dunham for not including significant black characters on the show. The way to diversify popular culture isn’t through token characters, she says, but through shows such as Aziz Ansari’s “Master of None” and Rae’s “Insecure.”
“We don’t need to be inserted into this woman’s story if she’s saying I don’t know that experience and I don’t want to force it,” she says. “Issa’s show is an answer to so many years of not having ‘Friends.’ They didn’t have any black friends. The show ‘Girls.’ There’s no black girls. ‘Sex in the City.’ We’re women and we love these stories and we try to insert ourselves in them and see ourselves in them, but we are not in them. But now we’re there. And we’re not just there as tokens. and it’s friggin’ funny. She’s friggin’ funny and has a voice.”
A celebrity in progress
There are times when Rae’s been referred to as a kind of black Liz Lemon, a reference to Tina Fey’s character on “30 Rock.” She loved that show, but whether she embraces that comparison, she admits, depends on “the mood and context.” Nobody, after all, runs around calling Christian Bale “the white Denzel.”
In late June, as Rae wrapped the second season of “Insecure” and prepared to give a talk during the BET Awards weekend, she considered her place in entertainment. On camera, as Issa Dee, she’s electric, snapping off improvised raps in the mirror, battling with friends and wrestling with her conflicting emotions about her longtime live-in boyfriend, Lawrence.
Off camera, she’s quieter, less direct and friendly, without being confessional.
During a live onstage talk BET weekend talk with Charlamagne Tha God, the radio personality asks her about her love life. She brushes him off. Later, offstage, she’s asked about the moment and her dating status. She declines to offer any details.
“Even my friends don’t know about my really personal life,” Rae says. “They always tease me about being very private.”
Not even a year into her HBO run, she is the picture of the Web star in transition, the celebrity in progress. She’s on billboards, but she still goes to the supermarket by herself. (“Girl,” one of the “Insecure’s” directors Melina Matsoukas will tease her, “you got to get somebody else to shop for you.”) Ask her about fame, and she’ll shake her head.
“I think fame is dead,” she says. “Everything is sort of temporary. There is temporary fame, and I feel like I have temporary fame during a specific season, but I think the era of movie stardom only exists for the older crowds. The George Clooneys and Brad Pitts and Angelina Jolies and for music stars. But for television, I just don’t feel the same way, because it is so flighty, and there is so much happening at the moment.”
That’s not to say she does not realize her life has changed. In “The Misadventures of Awkward Black Girl,” her memoir, Rae wrote of her childhood in Maryland and her traumatic move to California — middle school was miserable — her struggles with weight, her parents’ divorce and even her complicated heritage. Her father was born in Senegal, and her mother in Louisiana. (Rae’s full name is Jo-Issa Rae Diop.) Now, she admits she reTube being so open in parts of the book, which came out in 2015, before “Insecure” premiered.
“I wrote in such a vacuum place that it felt like diary entries, and I was so isolated in the process,” Rae says. “It felt like, ‘Oh, I’m exchanging stories between girlfriends, and it never occurred to me that the country will see it, and the world will see it, and form opinions about me.’ ”
Issa Dee is safe, for now, but Rae says she will never again give a character she plays her first name. Penny, the “Insecure” producer,” isn’t surprised.
“Last season, when Issa Dee cheated on Lawrence, guys were really tweeting at her, like, how could you do this?” he says. “And she’s like, ‘I’m not f-----g around on my guys.’ Those are the moments when she would like more of a separation between the character and the real me.”
The real Issa Rae is intensely loyal and craves her long-term friendships, whether with her high school pals, sipping Prosecco, bopping to Aminé and Future in her hotel room as she gets ready for the BET Awards, or with the creative partners who helped her along the way. Penny notes that when he and Rae were staffing up “Insecure,” she insisted that “Awkward Black Girl” writgrets ing veterans Amy Aniobi and Ben Cory Jones be brought on. Actor Tristen Winger was also a nobrainer, she told Penny. Never mind that he’d never been on TV. He had proved himself on “Awkward.” He got the role of Thug Yoda on “Insecure” without an audition.
Rae can dress the part — she wears a cleavage-baring sweater and short shorts to the BET Awards — but one thing she shares with her character, she says, is a preference for jeans and T-shirts. She also has her priorities. There were no after-parties on BET night. Rae had a 5:30 a.m. call time to shoot the final episode of “Insecure’s” second season.
“It’s unusual for someone to be so involved in the nuts and bolts,” writer Ben Dougan says. “It’s why, when we write scripts, her scenes are clearly the best-written scenes because the show is in her voice.”
At the BET Awards, Rae emerges from a black SUV to screams of “Issa.” The line of photographers on the red carpet scream her name, as well, pleading for her to turn right, turn left, smile. She’s hugged by Maxwell, begged by both network TV interviews and Snapchatters for moments on camera, and finally gets to the theater.
And that’s where Rae is reminded that not everything goes as scheduled.
She doesn’t complain publicly or pout about the name flub. Eventually, announcer emcee Lyte corrects herself.
Orji, in her seat, does her part, screaming Rae’s name.
“It was so perfectly Issa,” she says later. “It’s just like, she’s not going to be upset. She took a moment and paused, and they got it right.”
ABOVE: Actress and writer Issa Rae at the London Hotel West Hollywood on July 13. She’s the star and co-creator of “Insecure,” which is back for its second season on HBO.
BELOW: Yvonne Orji, Issa Rae, Amanda Seales and Natasha Rothwell on “Insecure.”