When Issa Rae’s viral web series The Mis-Adventures of Awkward Black Girl came to an end in 2013, fans of the YouTube project were devastated, wondering where we would get our next fix of the actor, writer, and creator. Rae’s internet debut, initially released in 2011, made a splash during a time when it seemed like everyone was creating web series, but the show stood out for its hilarious yet relatable depiction of life through the shenanigans of an awkward Black girl named J. Thankfully, we wouldn’t have to wait too long to see Rae on our screens again. Shortly after the series finale of ABG, she signed a deal with HBO to bring yet another important story to life: a new project titled Insecure.
Insecure premiered in 2016, and fans of Rae immediately recognised it as a natural continuation of J’s story. In this reimagining, the awkward Black girl was Issa Dee (Rae), a native Angeleno being swallowed whole by a very serious and scarily relatable quarter-life crisis. Stuck in a dead-end job complete with all of the microaggressions we’ve all experienced as Black women in white workspaces and an equally dead-end relationship with her long-term boyfriend (played by the ever-charming Jay Ellis), we met Issa at a point of distress as she tried to make sense of the rut she’d been in. At the same time, her best friend Molly Carter (Yvonne Orji) was navigating her own set of problems, balancing a rigorous career with a fruitless love life. For what seemed like the first time in years since the Golden Age of Black Hollywood in the 1990s and early 2000s, a nuanced and multi-faceted depiction of Blackness had once again taken centre stage.
As seasons continued, and Issa and Molly’s lives only got more complicated, viewers found themselves deeply immersed in Insecure’s plot, so much so that it took over our social media feeds and leaked into our group chats. Whether we were passionately debating who was responsible for Issa and Lawrence’s painful breakup (there is only one right answer here) or thirsting over Asian Bae as a community, we just couldn’t stop talking about Insecure. What started off as simply a fun show to fill our Sunday evenings had evolved into a fixture of Black millennial culture, a media moment so well-executed that it became a mirror reflection of its audience. From the characters, to their fashions, to their storylines, to the rich backdrop of L.A. itself, everything about Insecure felt like it was our story. These people were flawed — some, many would argue, far more than others — but each episode saw them learning and evolving, and their audience was growing up alongside them. The HBO series resonated with us because, whether we liked it or not, we had all been there; finally, there was a show made for everyone who was young, Black, and going through it.
After bringing us joy and a significant amount of strife for four seasons, Insecure will officially wrap after its fifth season, premiering in the UK on Sky Comedy on Tuesday 26th October. The announcement of the final season was heartbreaking for many of us, but all good things must come to an end. (Alleviating that pain is the fact that Rae and her production company Hoorae still have so much more content in the pipeline to share; earlier this year, Rae signed a $40 million deal with WarnerMedia that will allow Hoorae to create even more original series and films for us to obsess over.)
Ahead of the bittersweet final chapter of Issa and Molly’s tumultuous journeys, the R29Unbothered team is celebrating the show that brought the timeline and the culture together. Insecure, we won’t ever forget you… how about just one more season?
Brooke Obie, Deputy Director
“There’s something about seeing beautiful Black people lit properly and shot in HD! Before Insecure, I don’t think I have ever seen Black people look as beautiful on TV. Whether the characters were acting a hot mess or finally getting their lives together, to see us in our regular degular Black neighbourhoods and favourite hangout spots meant that there were people behind the scenes, behind the camera, in the writers room, who saw us and valued us and LOVED us. Insecure is a love letter to Black people, in all of our ordinary, magical glory. To Issa, Prentice Penny, the whole cast and crew, we’re sending the love right back.”
Insecure is a love letter to Black people, in all of our ordinary, magical glory.
Sandy Pierre, Branded Execution Specialist
“Where do I start with Insecure? First of all, Issa is my best friend in my head! I see so much of myself in her — not only as a dark-skinned woman, but also as an adult going through life and trying to figure it out. It was so important for me to have this show in my adult life. We haven’t seen a relatable Black show like this since The Game, Girlfriends or In Living Color. Insecure brought back normal Black working folks navigating through adulthood, relationships, career, etc. In a world full of reality TV (that isn’t real) and Black projects that just want to talk about enslaved people and killing Black men, Insecure has been a breath of fresh air.”
In a world full of reality TV (that isn’t real) and Black projects that just want to talk about enslaved people and killing Black men, Insecure has been a breath of fresh air.
Christa Eduafo, Social Content Strategist
“Pour one out for Insecure, one of the realest there ever was. I can’t recall another show that so accurately reflected my experience as a young Black woman trying to figure it all out. I saw myself in Molly, wanting to connect with someone but regularly playing in her own face. I saw myself in Issa, trying to build a life that felt fulfilling. I felt Issa’s Season 2 heartbreak over Lawrence ACUTELY as I went through my own break-up — we were swiping on Tinder together, chile. Watching Insecure over the years has truly been like going through my adult growing pains with a friend who has been through it all before. I’ll miss it, but I’m smiling because it happened! Cheers to Insecure.”
Watching Insecure over the years has truly been like going through my adult growing pains with a friend who has been through it all before.
Chelsea Sanders, VP of Multicultural Brand Strategy & Development
“I remember when Issa first started The Mis-Adventures of Awkward Black Girl on YouTube in 2011, I watched it and thought, ‘This is IT!’ Not just because it was Issa giving us her best Liz Lemon-meets-Maxine Shaw with a sprinkle of Joan Clayton on top. Not just because I too was a young Black 20-something in a questionable job with even more questionable co-workers and a love life that was mostly theoretical. Not just because Issa was from L.A. like me and casted friends I’d grown up with and gone to church with in the episodes. Yes, it was all those things, but more than that, quite simply, I loved it because it was just straight up GOOD ass content.”
I don’t know what we’re gonna do without this show, this vibe, or Molly to blame all our problems on, but I’m forever grateful that we had it because it just made me feel, well, a little less insecure.
“So when Insecure, ABG‘s grown and sexy auntie, first premiered, that’s exactly why I tuned in. Yet, somehow, Insecure was even better. From the L.A. landmarks and food spots I lived for to the time when Daniel (still fine!) said the now iconic line ‘All Black college educated girls listen to Drake,’ while he and Issa sat in the car listening to the Certified Lover Boy himself back in Season 1, it all just felt like me. I felt seen – exposed even – but in the best way possible, in the way that only content that’s made for you can make you feel. Embarrassed? At times. Hyped? No doubt. Screaming at the TV? For sure.”
“I don’t know what we’re gonna do without this show, this vibe, or Molly to blame all our problems on, but I’m forever grateful that we had it because it just made me feel, well, a little less insecure.”
Stephanie Long, Senior Editor
“Like Chelsea, my first introduction to Issa Rae was the 2000s YouTube sensation The Mis-Adventures of Awkward Black Girl. I am forever indebted to the boyfriend who put me on at the time, because if it weren’t for him, I would have missed out on what was undeniably one of the most important moments of Black girl visibility to ever happen on the internet. I saw so much of myself in J and the wobbly way in which she navigated some of the most uncomfortable situations. The amount of times I asked myself, ‘Why isn’t this on primetime television?!’ is too large to count. And then, in 2016, Insecure was born. For many, that’s where the legacy began. But for folks like me, Insecure has been a decade-long journey that started back in those ABG days, so it’s really weird to imagine the void that will be left once Insecure goes off air. The feeling is akin to that childhood friend you grew up with moving away to start a new life after decades of friendship. Okay, maybe I’m exaggerating, but I’m really going to miss the debates and camaraderie sparked by Insecure’s tantalising storyline.”
Premiering during the height of some of the most traumatic years the nation has had to endure, [Insecure] became a safe space in which Black folks could tune out the f**kery of it all and argue over whether or not Lawrence was worth the energy.
“Beyond that, Insecure really became a comfort of sorts. Premiering during the height of some of the most traumatic years the nation has had to endure, it became a safe space in which Black folks could tune out the f**kery of it all and argue over whether or not Lawrence was worth the energy (#TeamLawrence, don’t @ me, but we’re also Alexander Hodge stans over here, insert heart-eye emoji). It may be hyperbolic of me to say that I think I’m going to feel a bit lost without it once it’s gone, but thank goodness for streaming services, right?”
Venesa Coger, Style & Culture Specialist
“I love that Insecure didn’t hold back on how tricky navigating friendships, intimate relationships, and even what you want out of your career can be. The show depicted many accurate scenarios that actually play out in real life, and I believe that’s why so many people gravitated towards it. I’m going to miss being able to have a dialogue with friends about who is the better friend between Molly and Issa or trying to yell resolutions to their communication breakdown through the TV screen even though they can’t hear me. Insecure has definitely shown me the importance of looking at multiple sides of situations, not just my own — that’s what I appreciate the most from watching over the years.”
I’m going to miss being able to have a dialogue with friends about who is the better friend between Molly and Issa.
Maiya Carmichael, Social Coordinator
“Oh, Insecure…where do I start? I originally thought it was just a new cool show that came from a dope YouTube series, but as the seasons went on, I started to realise that it was so much more than that. Looking back on all the seasons, the show taught me that growth, change, and mistakes are all natural parts of life. And once you get through the hard times, there’s more than likely something better on the other side. If it wasn’t for Issa trying and failing at relationships (both her romantic partnerships and her friendships), I honestly would have been way harder on myself when I experienced these things in my own life. So, thank you Issa Rae and the cast of Insecure for wrapping up the crazy Black qualms of life and packaging them into five hilarious and emotional seasons, so that I could better navigate life.”
If it wasn’t for Issa trying and failing at relationships, I honestly would have been way harder on myself when I experienced these things in my own life.
Kathleen Newman-Bremang, Senior Editor
“Issa Rae recently told the New York Times that the goal of Insecure was to ‘elevate regular Black people and make us look as beautiful in our regularness as humanly possible.’ That’s a beautiful goal because insecurity was not associated with Black people on television before Insecure. As an insecure, awkward Black girl myself, this show was one of the first times I really truly saw myself on television. Through Issa Dee, I saw a Black woman who was flawed, messy and relatable. She made mistakes. She needed to spend an hour in front of the mirror to hype herself up before going outside. Every mirror rap, I felt that. It was through Issa Dee and her insecurity and her mistakes that Insecure broke boundaries. Insecure broke through the notion that Black Excellence is the only kind of Blackness we can see on television. Or that the only Black people worth watching were ones that were standing in direct opposition to the harmful stereotypes we’d seen for years. What Insecure did was not care about depicting exemplary Black people but just prioritising showing real, nuanced Black characters — specifically Black millennials — living their lives. I think it recaptured that essence that we lost when we lost shows like Moesha, Girlfriends and Martin for example, but it also gave us something we hadn’t seen before.”
The representation conversation can only go so far if there are only exceptions, and the rules stay the same. Issa Rae was an exception who has now set a new standard.
“We can’t talk about how much Insecure means to the culture, or to me personally, without talking about Issa Rae, the creator, the person, and the friend in my head. She exemplifies success in Hollywood because she is truly building an empire and changing what Hollywood looks like while she does it. I think the representation conversation can only go so far if there are only exceptions, and the rules stay the same. Issa Rae was an exception who has now set a new standard. In 2016 when Insecure debuted, the most popular shows were Game of Thrones, The Big Bang Theory, and The Walking Dead. We were craving something that depicted the Black experience in this kind of specific, fun and nuanced way. We were desperate for TV friends we could invest in that not only looked like us, but who felt real and layered. I spend way too much of my free time thinking about Issa and Molly’s friendship, the heart of Insecure and the relationship that catapulted this show from a funny comedy to one of the deepest reflections on female friendship in television history. There’s no going back to what television was like before Insecure, and Issa Rae is making sure of that. She, and the show, have launched the careers of other incredible Black creators like showrunner Prentice Penny, director Melina Mastoukas, producer Amy Aniobi, and powerhouse talents like Natasha Rothwell. The show’s legacy will live on in the work they will continue to give us for decades to come.”
Like what you see? How about some more R29 goodness, right here?