Issa Rae is hella cool.

Seriously, I’m not just saying that. Upon meeting her, she instantly puts you at ease despite me feeling both insecure and awkward (Come on, I had too.) If you think she's gone "Hollywood," she hasn't. Yes, your favorite actress, writer, director, producer and web series creator and now CoverGirl is extremely humble and gorgeous AF but that doesn't make her any less real. 

I shake Issa's hand for the first time on a high floor in the Empire State Building, overlooking Manhattan. And though I was ushered there in a luxury car, and even I'll admit it's a pretty glam location, Rae brings me right down to earth, asking, “Are you actually going to go back to work after this?” Alas, yes, I'm still working, so my Cinderella moment is short lived. But it seems like for Issa, the night at the ball has just begun.

We're meeting to discuss her new gig as a CoverGirl spokesmodel. Issa Rae is a new direction for the brand and quite atypical when you think about it. If you haven’t noticed, CoverGirl is undergoing a major makeover. They even switched up their signature tagline from “Easy, Breezy Beautiful CoverGirl” to “I Am What I Makeup” complete with new products to be unveiled in November. But, of all the numerous changes, we were most thrilled about the new roster of women of color representing the brand in 2017: Issa, Ayesha Curry and Massy Arias.

“[Being a CoverGirl] it feels magical. But I feel like this journey has kind of mirrored my own personal journey and my professional career in terms of finding my voice, finding my way and finding my face, and finding the way that I wanted to present myself to the world.” 

Of course, I was dying to know where she was when she found of the news. Not surprisingly, she was working.

“I was editing Insecure season 2 and I was extremely excited. I called my mom or was it my friends after work — I can’t remember who I called first. I was like, ‘This is really happening. This is really gonna go down,’ and I felt proud! I felt like this was a validation and really thought about like what I was going to be representing at the end of the day — and who I was going to be representing. And I think for me, the most impactful thing was actually the announcement and seeing how people really supported it and, you know, shared it, and they were rooting for me. That was just extremely, extremely touching.”

Issa joins the ranks of several Black CoverGirls before her, including Tyra Banks, Brandy, Queen Latifah, Rihanna, Paula Patton, Janelle Monáe and Zendaya as the brand continues to diversify it’s roster. I couldn't help but wonder if any congratulations came from her aforementioned predecessors. I mean, after all, it’s no surprise she has many celeb friends considering the epic Lemon Pepper Kickback party she threw in Atlanta earlier this month. 

“When [the news] came out, Janelle reached out. I spoke to her about her experience as a CoverGirl, feeling proud of her and never ever thinking I’d actually be one. I also was like, ‘Oh we’re the same skin tone, so I know who I’m going to look to for my products.’ She’s been super, super, supportive. Zendaya reached out today [October 23] and Queen Latifah had said great things. I saw her recently. I just talked to her on FaceTime via Regina Hall like two days ago. And then the new CoverGirls Ayesha and Massy who I’ve been following forever and now she follows me and I was like, ‘Girl, if you only knew!’”

Despite having her makeup done all the time now for appearances, red carpets, etc. [Editor’s Note: Issa works with Joanna Simkin often], she admittedly struggled a few beauty woes in the past.

“[In college] my girls were super girly and we were leaving campus to go to San Francisco to party getting all glammed up — and I wasn’t a makeup person. I didn’t want to get left behind, so I went to my nearest drugstore, grabbed makeup that probably wasn’t even my shade and didn’t know how to apply it. I put it on like lotion. [Laughs] I looked a hot s**tty mess and, thankfully my girls were very honest, like, ‘Girl, no! Don’t!’ Thankfully, one of my friends helped to do my makeup. But [at that moment] I was like, ‘I need to do better and I need to learn!’”

Now Issa counts CoverGirl’s Healthy Elixir Foundation in Soft Sable as her savior and uses a beauty blender versus brushes for a flawless beat. “I can’t use brushes. I don’t identify with being a painter. I could never draw, and so to draw on my face is just not happening. I’ve tried and it works to a degree, but I love using that in combination. Joanna’s really helped to accentuate my eyes in a way that I really like. When I do it myself, I put on liner and, of course, eye lashes. I love the way that she does my eyebrows, so that’s been a new focus for me.” 

While her new campaign products are under wraps — hint, they drop on Cyber Monday — I couldn’t leave without asking Issa about when she feels the most beautiful. Was it during her sultry scenes with Daniel or Lawrence (on Insecure)? Was it when she covered AdWeek? Was it at the Emmy’s when she told us she was “rooting for everybody Black” in custom Vera Wang?

“This is corny, but I feel the most hella beautiful when I’m shooting the show, putting it together and editing it,” she says. “That’s when I feel hella beautiful, because I remember when I wrote this and shot it. And now it’s a product that people are going to see, like, that feels beautiful. It makes me feel so, so confident.”