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True Issa Rae fans remember her from The Misadventures of Awkward Black Girl web series. Rae portrayed J, an off-beat 20-something who made life cloddish, one situation at a time. She was a comedic superhero for the Black women who identified as socially awkward over-thinkers. Her iconic mirror raps were birthed in the first episode of the series, and it set the tone for the quick-witted freestyle artist whose flow got activated during almost every hiccup in her life.

J’s character did not exist in the world of media until The Misadventures of Awkward Black Girl. Her ability to connect to an entire community of women who went unseen for so long was the beginning of her promising reign in the entertainment industry.

When Rae premiered her hit HBO series Insecure, she had no idea it would take off the way it did. It was then the world understood just how talented and hilarious the writer and producer really is. Watching her career reach new heights is kryptonite to creatives eager to see their dreams go from an idea to an award-winning vision. Since her reign, the 38-year-old visionary has written, directed, and produced a few TV series and movies, written a New York Times Bestseller, launched her own Prosecco, co-founded a natural haircare line, and opened her fourth coffee shop.

And if you need more motivation to get your life together, Rae dropped a viral video that outlines her approach to 2024. She oozes Capricorn energy in all its glory. The California native has a high aptitude for success, and it is inspiring. She is a testament to creating your lane and dominating it with ease. Today, the revered mastermind turns 39 years old. In honor of her solar return, here are five times Issa Rae proved she is the creative genius of our generation.

5 Times Issa Rae Proved She Is The Creative Genius Of Our Generation

5 Times Issa Rae Proved She Is The Creative Genius Of Our Generation  was originally published on

1. Insecure

Insecure Source:HBO

Perhaps Rae’s biggest claim to fame is the iconic show Insecure, which ran a total of 5 seasons before she threw in the towel to focus on other projects. The culture-shifting series followed Rae’s character, Issa Dee, and her evolution through friendships, relationships, and career goals. Each season, the show took on a life of its own, expanding into meaningful conversations like postpartum depression, gentrification, and the importance of stepping out on faith despite the blunders during life’s journey.

The #TeamLawrence vs #TeamIssa debate divided couples, and the #TeamIssa vs. #TeamMolly controversy had people examining their friendships. More importantly, the show forged a sense of community among watchers, who would celebrate each premiere with watch parties and live-tweet each episode in real time.

The show has received countless award nominations, including the Golden Globe for Best Actress in a Television Series, a few Primetime Emmy awards, Critic’s Choice awards, and more.

Rae procured five NAACP Image Awards, an AAFCA Award, a Peabody Award, and two NAMIC Vision Awards. The cast has been nominated and won various awards as well. Insecure is responsible for launching acting careers, putting more Black writers in the writer’s room, and expanding the cast’s experience by putting them in the position to direct episodes. 

2. Sienna Naturals

Rae has put on for the natural girlies since she stepped on the scene. Her allegiance to natural hairstyles has inspired women to embrace their texture while experimenting with different looks no matter the occasion.

In 2020, Rae became the face and co-owner of the clean and vegan haircare brand Sienna Naturals. Together with her long-time friend and sister-in-law, Hannah Diop, they’ve developed a clinically-proven product line that revitalizes your hair by restoring moisture, one strand at a time.

Sienna Naturals is one of the eight brands to join Sephora’s 2024 Accelerate Program, “a brand incubation program dedicated to building a community of innovative, inspirational brand founders in beauty,” according to

3. Hilltop Coffee + Kitchen

No one rides for LA like Rae. In many ways, Insecure was a love letter to the city, much like Sex and the City was to New York City. Through her show, she highlighted the good, the bad, and the ugly of the City of Angels, but she mainly highlighted the wealth of creativity found in every crevice of the various neighborhoods. 

The entrepreneur is leaving her mark on LA with Hilltop Coffee + Kitchen, a business venture she joined in 2019 when she assisted the owners, Yonnie Hagos and Ajay Relan, in opening the first location in the Inglewood neighborhood. They later opened locations in Slauston, Eagle Rock, and Downtown LA.

4. Viarae Wines

If the writer’s strike taught us anything, it’s that the vision should be bigger than the media world if you desire a sustainable career. When shows were on pause, Rae tapped into her creative bag and developed Viarae Wines, a sparkling Prosecco that sold out almost immediately after its release.

5. HOORAE Media

And if you need more proof that Issa Rae is that chick, look at this clip. The Rap Sh!t creator has a significant hand in telling Black stories and pushing Black creativity. Through her broadcasting and media production company, she controls the narrative of the Black experience. Both Insecure and A Black Lady Sketch Show are produced by HOORAE and HBO. The HBOMax series Rap Sh!t and the revival of Project Greenlight are also produced by Rae’s company.