“Wings and Prosecco, Baby”: Issa Rae Gets Real About Success, Super Bowl Plans, And Still Being An Awkward Black Girl – Essence

When you think of Issa Rae, you might picture the life of the party (especially if you’re like me and used to watch from afar as she used to host those epic #yachtshit parties).

After all, she is the Hollywood “it” girl who turned her awkward moments into Emmy-nominated television (and arguably one of the greatest shows of all time), and then parlayed that success into a growing business empire spanning entertainment, beauty, and spirits. But the real Issa? She’s still figuring out where she’s watching the Super Bowl.

“I’m trying to find a couch,” she tells me with a laugh. “I was thinking about hosting, but then I don’t feel like cleaning up after. So I’m trying to dirty up somebody else’s house and bring, of course, all the snacks and accommodations.”

Her Super Bowl spread will be a perfect reflection of her evolution from relatable storyteller to luxury brand founder: “Wings and Prosecco, baby. I’m from both worlds now,” she says, likely referring to her own Prosecco line, Viarae. And like many casual football fans, she’s perfected the art of selective engagement: “I love a good final quarter. So that’s when I tune in where I’m like, ‘oh, I’ve been paying attention the whole time’ when it’s really, really stressful.”

The occasion for our chat is Rae’s first-ever Super Bowl commercial for TurboTax, but our conversation reveals something more interesting about one of entertainment’s most influential voices: how she’s learned to face challenges head-on, whether it’s finances or fitness.

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“Before I used to avoid it because money is hard, filing taxes is hard,” she admits about her early career days. “I remember as soon as I had a job where… I was out of college and I had to actually file my taxes, I put it off. I was like, ‘Well, how are they going to know?’ And they know. They know.”

That same determination to tackle things differently shows up in unexpected places. “I never thought that I’d be a runner because it’s just, it’s hard,” she shares. “I was like, I got to run outside. What if it’s hot? What if it’s raining, my knees, all that. And then once I got a treadmill, now I love running and it’s become part of my kind of meditative process.” When asked if we might see her in a run club or marathon soon, she laughs it off – though with a Capricorn’s characteristic determination, she won’t completely rule it out.

As she continues building her entertainment portfolio, including the recent release of One of Them Days starring Keke Palmer and SZA, Rae’s got her sights set on a dream collaboration. “I really want to work with Regina Hall in a comedic movie,” she reveals. “She was one of the first, I guess I would say, celebrities that I ever co-wrote a project with. And we just never got a chance to make it… I always hit her every year, ‘Girl, I’m working on it.’ And she’s like, ‘Okay, well where is it?’”

In a time when the entertainment industry and world at large feel particularly chaotic, Rae has found her own way to maintain balance. “I think it’s good and bad, but tuning out like so many other people are, and just focusing on literally the things that do bring me joy and finding inspiration in the little things,” she explains. “For me, my work is an escape and I’m fortunate enough to be able to tune it out and just figure out how to help in my own community in my own ways. And that’s the only way that I’m able to stay kind of sane.”

Despite her growing empire and larger-than-life public persona, Rae is quick to dispel one common misconception. “People assume that I’m like the life of a party when I’m just really so quiet and I have to be comfortable in my zone,” she says. “People have developed this like, ‘You know how to party personality’ and I’m like, ‘Oh, no. I’m literally still an awkward Black girl. I just got to be comfortable.’”

This year she wants to help emerging creatives and entrepreneurs file taxes easier and more stress free than ever. After all, her financial advice comes from personal experience: “If you’re not willing to invest in yourself, you can’t ask anybody else to invest in you… Sometimes creatives will look for that money up front because they don’t have it, but also to just save. Save, as you do have a job, put a little money aside.” She adds with characteristic honesty, “Unfortunately, I went into credit card debt, buying a camera ultimately, but it paid off. I think just being smart about the money that you’re putting aside to pursue your creative endeavors.”