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Insecure Season 5 premiere assets

Source: HBO / HBO

Growth, okay?!

Season 5 came at us fast, didn’t it? The final stretch of Insecure took us through a worldwind of emotions, but it also taught us so much about life, love, friendships, careers, family and more.

Season 1, episode 1 begins on Issa Dee’s birthday. As she’s at work dodging insulting questions from inquisitively rude teenagers, she realizes that age 29, she’s not doing what she loves, she’s in a 5 year potentially dead end relationship, and she’s ready for something to change. She’s completely insecure about her current stage in life, and we get to watch her figure it all out. Over the course of 6 years, Issa Rae’s character grows and stretches in ways that catapulted her into the securely insecure boss we meet in season 5.

Through her art, Rae told the story of two 30 somethings (Molly and Issa), trying to manage a hectic life in Los Angeles. Through good advice, bad advice, growing pains, career level-ups, career f*ck ups, and more, they end up exactly where they’re supposed to be in life – reinforcing the idea that the journey is just as important as the destination.

The show shifted the culture in such a groundbreaking way. For 5 seasons, we fell in love and identified with fictional characters that somehow represented an entire generation. Chef’s kiss to the show that single handedly changed the way we were perceived on screen. Kudos to the series that showed the many ways a boss can look. From Molly’s HBIC lawyer energy to Dee’s entrepreneurial spirit, we got to see why the world needs both.

There are so many reasons why this show is important to Black culture. Insecure is an alluring taste of the modern-day Black renaissance, as told through the eyes of Rae, her many talented writers, her director, and the actors and actresses who have now become our family. In honor of the series finale, we’re discussing 5 ways Insecure was the revolutionary art our generation needed.

5. Issa showed modern-day Black women living in luxury.

Insecure Season 5 premiere assets

Source: Glen Wilson/HBO / Glen Wilson/HBO

We’ve had examples of Black women living in luxury, but never like this. Although we see the social and career highs of each individual woman, Dee’s glow up is an inspiration to anyone who wants more in their life. During episode 1 of season 1, Dee asks herself, “How different would my life be if I actually went after what I wanted?” Although she asks herself that question as she reflects on Daniel’s big ole chocolatey self, it looks like subconsciously she harps on that question throughout each season simultaneously, as she pursues her dreams. From “We Got Ya’ll” to an entrepreneur showcasing the best talent LA has to offer, Dee shows that anything you want in life IS attainable. The career, the relationship, the friendships; all of it.

Dee’s friend circle matched her fly. Molly, described as the Will Smith of the corporate world, is a code switching lawyer that likely has never owned anything from The Gap or Old Navy. She lives in luxury because she knows she deserves it. It’s a mood, to be honest. Both Kelli and Tiffany are business professionals that live financially comfortable lifestyles as well.

4. She created a team that reflected her, then she passed the baton.

Not only has the show changed the culture, Rae has made it a point to pass the baton on to people interested in writing, and producing, and she’s been instrumental in extending opportunities to all women, but specifically women of color. Rae has continuously promoted her staff and given them new opportunities that they may have never had access to. People who started as PA’s are now show runners in other Rae Production projects. Not only were people on the backend of the show able to level up, stars like Yvonne Orji and Natasha Rothwell were able to score some major opportunities thanks to their visibility on the show.

Let’s not forget the slew of Black designers featured on all 5 seasons of Insecure. The dedication to promoting all things Black was loud and clear. In her now infamous catchphrase, “I’m rooting for everyone Black,” Rae and her team definitely put their money where their mouth is.

3. She showed the beauty of Los Angeles

Insecure Season 5 assets

Source: Merie Wallace/HBO / Merie Wallace/HBO

I know I’m not the only person who has a photo of themselves in front of The Dunes. I’ll take it a step further and say I don’t have the traditional LA photos of the Hollywood sign or other popular landmarks. Issa Rae showed the beautifully Black neighborhoods, Black-owned businesses, and all of the amazing Black talent LA had to offer. For years, Black neighborhoods in LA were portrayed in a negative light. Not only does she shed light in the recent spike of gentrification, she took us into the Black neighborhoods and showed off the Pilars and gems that make these spaces worth visiting.


2. She showed the beauty in sisterhood

Insecure Season 5 assets

Source: Merie Wallace/HBO / Merie Wallace/HBO

Issa, Molly, Tiffany, and Kelli represented true and authentic friendships. Each woman carried a genuine love for each other, and it honestly taught our culture the importance of communication, unconditional love, grace, community, and understanding. While we see discord between the friend group play out in season 4, the ladies were able to bounce back in such a needed way. Even though we watch both Molly and Issa get their men by the end of season 5, the true love story is between both characters. They are each other’s soulmates.

1. She went from YouTube to an Award-winning show

We are privileged to watch Rae’s career grow from YouTube to an Award-winning actress, writer, producer and director. If you followed her from her Awkward Black Girl days, then watching her end the season of a show that knocked our entire planet off it’s axis is pretty exciting. Not only did she win, WE won. We got to see our stories play out on screen. We got to tackle important issues within the Black community like mental health stigmas, postpartum depression, living out your hoe phase, weighing career options, deciding to work for a Black company vs a White one, hell, even having someone ejaculate in your eye. These stories, our stories, were told by us and played out on screen by people who looked like us. We got to have beautifully chocolate men and women play the lead and love interest.

Her career trajectory is impressive. She’s created a roadmap to success and she’s continued to extend her hands and bring her people along for the ride. Rae recently inked a new five-year deal with HBO’s parent company WarnerMedia to produce a number of new shows and movies. In short, Rae is just beginning.


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The End Of An Era: 5 Times Insecure Was The Revolutionary Art Our Generation Needed  was originally published on