Issa Rae: From Awkward Black Girl to Hollywood’s Coolest Queen Boss

If “glow-up” had a face, it would be Issa Rae in a power suit, holding a mic in one hand and a film script in the other. From YouTube star to media mogul, Issa has gone from “hella awkward” to hella influential—and she’s just getting started.

Let’s take a joyful stroll down memory lane (cue the Insecure soundtrack)...

It All Started with a Little Awkwardness...

Back in 2011, Issa Rae was the internet’s best-kept secret with her hilarious and painfully relatable YouTube series, "The Misadventures of Awkward Black Girl."

She played J—an awkward, quirky Black girl just trying to survive the office, dating, and life. It was weird, wonderful, and unapologetically Black—and it went viral. Like, “I just binge-watched this entire season on my phone in bed” viral.

Issa didn’t just break the internet—she cracked the code. And Hollywood finally took notice.

Then Came Insecure… and Everything Changed

In 2016, she hit HBO with the cultural phenomenon known as Insecure—a show that gave us edge control, mirror raps, messy besties, and deep convos about adulting in L.A. The show ran for 5 unforgettable seasons, racked up Emmy nominations, and gave Black women a show that felt like home.

Issa Rae didn’t just play a role—she created a world. One where we could be awkward, loud, introverted, successful, struggling, soft, complicated… and still be fly.

🎥 But Wait—There’s More...

Since Insecure, Issa’s been booked and busy with:

• Her production company, HOORAE Media, producing content that centers Black voices across film, TV, music, and digital media.

• Acting roles in hit films like The Photograph, Vengeance, Barbie (yes, she was President Barbie), and American Fiction.

• Producing hit shows like Rap Sh!t on Max, a hilarious yet gritty look at two Miami women trying to make it in the rap game.

• Launching a record label and backing artists like Yung Baby Tate and Josh Levi.

• Opening a coffee shop, Hilltop, and building a thriving business hub in South LA.

• Becoming a voice in the tech world, investing in Black-owned apps and advocating for equity in Hollywood and beyond.

  
  

Sis really said “multiple streams of income” and meant it.

Issa the Icon

Let’s be real—Issa Rae didn’t just “make it.” She kicked the doors down, flipped the Hollywood table, and built her own.

She’s the queen of telling stories that feel like us: awkward, funny, sometimes tragic, always beautiful. And she's all about uplifting other Black creatives, not just being the token in the room.

"I’m rooting for everybody Black."– Issa Rae, forever mood.

What’s Next?

Between executive producing, acting, building an empire, and being the flyest introvert in the game… who knows? Maybe her own podcast? A directorial debut? A makeup line? A Wakanda reboot?

All we know is: whatever Issa does next, it’ll be bold, Black, and brilliant.

Stay Rooted, Stay Real

Issa Rae is proof that being yourself is your superpower. She didn’t wait for Hollywood to come calling—she called herself, created her own lane, and brought the whole culture with her.

**Visit **QueenPinsMedia.com to keep up with more powerful Black women rewriting the rules and crowning their content across the media world. ✨