Five minutes with Issa Rae at Miami Art Basel


The Versace Mansion in Miami’s South Beach is, in theory, a morbid place to party. Gianni Versace was murdered here, shot on the steps in 1997 by 27-year-old Andrew Cunanan, so it is weirdly dichotomous to see Issa Rae, Insecure star and showrunner, necking back a bubbly mix of gin and champagne at Artsy’s party to celebrate the finalists of Bombay Sapphire’s Artisan Series, a competition for emerging artists. There are parties at the Versace Mansion—now a hotel called Villa Casa Casuarina—all the time.

Clad in a mustard ALC dress over matching pleated pants—she likes “a bit of a casual slay”—Rae’s look worked with the very glamorous surroundings. It doesn’t make for a very Versace outfit (when were Gianni or Donatella ever casual?), but does clearly describe both Rae’s style and that of her semi-autobiographical Insecure character, Issa Dee.

Rae, 32, is certainly having a moment. There’s the major success of Insecure, a show about young black people in Los Angeles and their sex and dating lives. Then there’s Rae’s first movie role as an activist in the upcoming The Hate U Give, based on author Angie Thomas’s YA sensation. We sat down with her to talk about partying with Samuel L. Jackson, mixing wines and liquor, and the persistent annoyance of #LawrenceHive, the fans who stan for Insecure Issa’s fuckboy-esque ex-boyfriend.


JOCELYN SILVER: How’s your Art Basel going? Have you been before?

ISSA RAE: No, this is my first time. I just learned how to pronounce Basel.

SILVER: To be safe I just say Art Week.

RAE: I saw that and it’s such a cheat! Like, I could have been saying Art Week the whole time?

SILVER: Such a cheat. What kind of art draws you in?

RAE: I like anything that ignites something in me. Like, “Oh, this feels nostalgic, or I can understand the artist’s point of view.” I look at this party in particular, or other events this week, and I like that the artist can basically tell you what they’re thinking. Although a lot of the fun is in interpreting the work. It’s so deeply personal to people who view the art, who make the art. Everyone has their own subjective experience.

SILVER: I’m obsessed with your Instagram. I remember a few months ago you were posting from the craziest party with Girls Trip breakout Tiffany Haddish. Can you tell me about that night?

RAE: Yeah! So me and Yvonne [Orji, who plays Molly on Insecure] were filming in Atlanta at the same time, and we were just hitting each other up. We only got to see each other once—basically just at that party, which is insane. So we kept on texting, and she was like, “There’s hella people out here,” so we just decided to have a party and invite all our friends.

I love throwing house parties because I don’t like to go out. And then so many dope people came. Samuel L. Jackson came!

SILVER: What is it like to party with Samuel L. Jackson?

RAE: He was just cool! He was like, “You’re a cool homie.” He was just super honest, down to earth. Everybody was down to earth.

SILVER: Does Samuel L. Jackson watch Insecure?

RAE: Yeah!

SILVER: Is he #LawrenceHive?

RAE: I didn’t ask him that! I didn’t want my feelings hurt. [laughs] We were vibing. He’s been watching my stuff for a long time. I used to do this video series called “Ratchetpiece Theatre,” and he shouted that out years ago. I was dead.

SILVER: You said you don’t like going out. How do you deal with all the parties at Basel?

RAE: I bring my friends and then everything is wonderful. And then I have alcohol and it’s like, “I was born to do this.”

SILVER: Every Sunday night, when Insecure is airing, there’s an insane storm on Twitter. How do you deal with that?

RAE: It’s so much fun! That’s what you dream of. But it’s annoying when people confuse you with the character. Even today, somebody was like, “Okay, let’s just say four months ago Issa got cum on her face … let’s not forget that.” I’m like, “I guess it’s cool if you want to commemorate that!” But it is so cool for people to be so involved with something that I get to make with people that I love.

SILVER: The cum moment was wild. First of all, it was a piña colada, right?

RAE: Yes, it was delicious.

SILVER: And that episode [“Hella Blows,” which devoted a big chunk of the plot to conversations about black women and the implications of performing oral sex] was the most controversial of the season. How did you deal with that one?

RAE: It was interesting, because it was one of those things where you wish that people were privy to the conversations we were having, the thought processes behind it. We’re also trying to tell a larger story. The conversations we were having about blowjobs were about so much more than just blowjobs, you know?

A lot of our show you can take at face value, but we’re always trying to build something underlying. That episode was definitely a big learning lesson, just in terms of how we tell stories. It just showed us how closely people watch the show—which is a compliment—but also scary.

SILVER: You host the Insecure after-show Wine Downs. Is wine your favorite drink?

RAE: I’m much more of a prosecco person. I love sparkling wine, I love champagne. And I love bourbon. So I mix them together.

SILVER: You mix prosecco and bourbon?

RAE: Yeah, or prosecco and whiskey. Just a splash.

SILVER: I like that.

RAE: What’s your whiskey of choice?

SILVER: Maker’s Mark, generally. Is that bad?

RAE: No, I like Maker’s Mark. It’s like, affordable bougie.

SILVER: When you watch the Wine Downs with Jay Ellis [who plays Insecure’s Lawrence] and other male actors on the show, they are very #LawrenceHive. Is that annoying?

RAE: Well Y’lan [Noel, who plays Daniel] is very #DanielHive. He’s such a good actor, he has such an interesting interpretation of Daniel. But they all just have such deep allegiances to their characters, which is very sad. [laughs] I can see why people are #LawrenceHive, but Jay cannot see why people would be #IssaHive.

SILVER: Well whatever. Issa forever.