BY EMILY MAHANEY
Last July, I screened the pilot of Insecure, the HBO comedy about two best friends, Issa and Molly, who are unsettled and on the cusp of 30. In that episode Issa takes Molly, who’s crying “tears of singleness,” to an open mic night to cheer her up—and proceeds to take the stage and perform a freestyle rap called “Broken Pussy,” based on Molly’s inability to keep a dude. It kills. Like Molly, I was in my late twenties and aggressively single at the time, and I laugh-cried on my couch...alone...on a Saturday night watching the scene. The girls are real, the writing is sharp, the jokes land, and the look is lush.
So who’s behind all that magic? Issa Rae (who made a name for herself on YouTube with The Misadventures of Awkward Black Girl) cocreated the show with Larry Wilmore and sold it to HBO when she was just 28. Rae—who writes, stars in, and produces—then tapped fellow TV first-timer Melina Matsoukas, known for music videos like Rihanna’s “We Found Love,” to direct and later produce. (You can also thank Matsoukas for directing Beyoncé’s “Formation” video.) Together these two revolutionaries and fast friends have told a new kind of story about female identity and black female identity.
Now the series—which earned Rae her first Golden Globe nod last winter—is wrapping up its second season. Fresh off a life-changing breakup, Issa (Rae) is running her vibrator out of batteries; meanwhile, power lawyer Molly (Yvonne Orji) sees her world turned upside down after she opens a male colleague’s massive check by accident. Their friendship? It’s what’s holding them together.
As for Rae and Matsoukas, they’re as unstoppable as ever.
GLAMOUR: How did this friendship, and partnership, come to be?
ISSA RAE: I started out as a fan, watching Melina’s music videos. I put her name on the list for the show early on, and because of her nonexperience in TV, it was kind of overlooked. Until it wasn’t, and HBO was like, “Yo, you wanna take a risk? Who you want?”
MELINA MATSOUKAS: I remember our first Skype call was terrible. But two days later we were in a room, and we spoke the same language. We’re both black women navigating the world, having to code-switch and figure out how and where we fit in.
ISSA: There was a familiarity, “I don’t know you, but I know you.” After I left that meeting with Melina, I danced in the elevator.
MELINA: I remember going to HBO, and the president at the time was like, “We don’t normally do this.” Meaning: give a first-time creator, a first-time director, and a first-time showrunner [Prentice Penny] an opportunity to do it together. “But let’s do it.” It was because of Issa that I was even in that room. She’s paving the way for young female filmmakers and filmmakers of color.
ISSA: Then we went to sushi—
MELINA: She got me drunk. And wrote all my stories into seasons one and two!
ISSA: You’re such a liar! I’d never really gotten a chance to work with someone who challenges while being collaborative. Especially being a woman of color, sometimes it’s hard for us to put our foot down. You work with a lot of men, and they’ll be like, “She has the reputation for being kind of a [makes a disapproving noise].” Melina knows what she wants and has an excellent reputation.
MELINA: Issa is redefining the black female identity on television. I don’t think we’ve ever seen a more basic character than Issa Dee. As black women, we can never just be regular—have flaws, be vulnerable, be a hypocrite, whatever. She’s shown us that person; I don’t know if we have seen that on television before.
GLAMOUR: Let’s talk about season two: Molly and Issa’s relationship is really the relationship. Were there any tropes about female friendships, or about black female friendships, that you were trying to disrupt with the show?
ISSA: In a lot of the shows that I'm still a fan of, like Love & Hip Hop, Basketball Wives, and The Real Housewives, there’s a lot of tension between women of color. We live off the drama and the fights, but that’s not all female friendships.
MELINA: We’re also showing that your soulmate is sometimes your best friend. That your female friendships can be just as fulfilling as [romantic] relationships, if not more.
GLAMOUR: This season Molly opens her white colleague’s check by accident and sees that he’s getting this jaw-dropping amount of money. Why did you want to dig into the issue of pay equity?
ISSA: It’s just something that’s real: Women are paid less than men, despite the fact that that’s illegal. Black women, specifically, are paid less than white women. It’s something that we wanted to address: She is great at her job, so why would they undervalue her?
GLAMOUR: Another moment I loved: Issa starts using her vibrator, then it dies. That scene is cool because it shows raw female desire. She runs around the apartment looking for batteries so she can pleasure herself; she wasn’t running around to get a condom so she could have sex with a guy. How did that scene come about?
ISSA: In the [writers’] room we were talking about what it feels like to be thirsty and how we don’t really get to see female characters masturbate. Even in a funny way. Especially black women! So we wanted to portray that, while remaining true to our show and showing sexual frustration.
GLAMOUR: Both Molly and Issa are single. What challenges do you see women, and black women in particular, facing in the dating world, and how do those experiences inform this season?
ISSA: We’re combating being undesirable. That’s a lot of the narrative: that black women are undesirable. Every day an athlete or a rapper says something along the lines of “That’s why I don’t date black women.” Like Kodak Black—your name is Kodak Black and you don’t f-ck with black women? OK, cool.
MELINA: Stay over there!
ISSA: We’re showing that these women are desirable. But Melina, you always say, “This is L.A. How are they getting so many dates?”
MELINA: Sometimes I’m like, Y’all wrote this black woman’s wet dream, where you have this fine-ass dude stalking you, calling you, but you’re not calling him. That’s not real life, but...
ISSA: L.A. dating: People feel they can always do better.
GLAMOUR: There are so many things that the white characters do and say in Insecure that make me, as a white woman, cringe.
MELINA: And you’re like, “Do I do that?”
GLAMOUR: [Laughs.] And by bringing humor to it, you can easily call it out: “Stop doing this—”
MELINA: Right, don’t touch my hair. You need humor to deal with these obstacles, whether it’s racism or sexism. It is easier for people to understand and accept [that criticism] when there’s humor in it.
GLAMOUR: As I look at the credits, I see a lot of women’s names. What is the staffing like behind the scenes?
MELINA: Our story is rooted in authenticity, and our stories are best told by the people they are about, you know?
ISSA: There’s a lot of sex this season. When I’m in the writers’ room, I dissociate myself: “Let’s have Issa do this!” By the time I’m shooting, I’m like, “Aww, f-ck! Igotta do this shit?” I’m still a regular-ass person who gets embarrassed and shy. It’s more comfortable to be around a woman director.
GLAMOUR: Is there mentoring going on behind the scenes?
MELINA: It’s such a priority for us. We have a shadowing director on every episode. The person is literally like a shadow to the director.
GLAMOUR: Kerry Washington was one, right? What was that like?
MELINA: Crazy. My friend was like, “Was Kerry Washington your intern?” I’m like, “She wasn’t my intern.” [Laughs.] She wants to direct, and she asked if she could come and learn. She was a total student. But we also have young filmmakers who shadow the crew. We’re trying to be that school, as we’re learning ourselves.
GLAMOUR: You have a number of celebrity fans, including Sterling K. Brown, who guest-stars this season.
ISSA: At an event he said, “I love the show, if you ever need....” I was thinking, Ha-ha, he’s just being polite. A few months later, he slid into my DMs: “These are my free days, if you have anything!” I was like, What? We had the perfect role. Every woman who watched his scenes on the monitors had a pasted-on smile—he’s dreamy.
GLAMOUR: And President Obama told you he liked the show too. What was it like to meet him?
ISSA: I brought my mom to a party at the White House. She got to the front of the line and got a hug from him. Then I got in line with Yvonne [who plays Molly]. The president held my hand and said to Yvonne, “Oh, she’s having a good year!” I was like, “The President knows me?” We started screaming! He was like, “I love the show and the soundtrack, and I love to see black women being creative.” I walked away and collapsed to my knees. [Laughs.] My mom missed the whole thing. She was so busy obsessing over her hug. She was like, “What did I miss?” Mom, you missed everything!
GLAMOUR: So many women—black, Latina, white—relate to the characters in this show. What should that say to Hollywood execs?
MELINA: That you don’t have to be one color to relate to a story. I grew up watching a lot of non-people-of-color whose stories I related to in my way. But everybody’s worth is as important as the next person. And we need stories that are different. Understanding about other people leads to acceptance, which is something that we need desperately.
Bonus Round! Here Are the Best Practices for Working with a Friend, According to Issa Rae
Don’t beat around the bush.
“Melina and I are really straightforward with each other. We’re both clear and passionate about our points.”
Swallow your nos.
“I’m always tempted to say, ‘Nah, that won’t work.’ But I think you should be willing to try ideas
out before saying no. Be open-minded.”
Save your fight.
“If something is important to Melina and not all that important to me, I let her win. ‘You can have this one thing; just know I’m gonna ask for my one thing a few days from now!’”
Give props where props are due.
“I tell her when an idea is great right away: Usually it’s a ‘Yaaasss, you did that, you did that!’ I’ll dance. I will sing.”
Encourage her to live.
“I recognize you need a personal life: Take your vacation, go hang out with your man, have fun! I’m gonna have your back, and you’ll have mine."