"Since Yvette Lee Bowser’s Khadijah housed her wild friends in her luxurious New York apartment on Living Single, which kicked off in 1993 (a full year before Friends), Black friends on television invited young Black adults to compare their professional progress, the sincerity of their lovers, and the strengths of their friendships with what they saw onscreen," says Joelle Monique. "It happened again in 2000 with Mara Brock Akil’s Girlfriends: Four women at different professional, romantic, and spiritual stages of life relied primarily on their friendships to get them through the hard times. While many iterations of the friendship sitcom exist, a Black woman invented the genre as we know it today, and a Black woman perfected it with Insecure. For a demographic that can boast most educated in the United States and the least desired for marriage, it’s fitting that decade after decade, Black women revisit and reevaluate these cherished relationships with one another on high-profile shows. Before Bowser, sitcoms mostly focused on workplaces, educational institutions, or families, with some outliers like The Odd Couple, Three’s Company, and Golden Girls. These shows focused on the absurdity of these people being friends, centered around the final years of life, or relied on sexual innuendo—or in the case of Golden Girls, all of the above. Before the mid-’90s, most people in their late twenties were married with children or divorced. But as young people began to establish careers before walking down the aisle, the role of friends started to take center stage earlier in life. Friends held holiday dinners, watched over parents when they became ill, and stayed up all night after tragedy struck. Perhaps there was a fifth friend in the Insecure group: the audience. The late bell hooks told us, 'Loving friendships provide us with a space to experience the joy of community in a relationship where we learn to process all our issues, to cope with differences and conflict while staying connected.' Issa Dee attempted to escape reality throughout the entire series. She tried to imagine she could say what she really wanted to say to an enemy, or the different possibilities of a career choice, but the moments deeply embedded in reality—her long walk with Molly around their old campus, sitting alone on the couch that once represented the endless possibilities of new love and now presented a conclusive end to that love—linger in the minds of viewers, and challenge them to face their own insecurities. Insecure showed that doing the internal work leads to the eternal reward of loving friendships. Behind the scenes, it taught Hollywood to look for Black talent because it’s available in abundance. Listen to the impossibly excellent Insecure Playlist on Spotify, or note the ascension of Natasha Rothwell as one of the most promising writer/actors in the industry, or the emergence of showrunner Prentice Penny as a guiding figure in Black television excellence. A TV show cannot be a friend, but sometimes it can feel like one; it can bring you closer to an old friend, or encourage you to seek a new one. Sometimes, saying goodbye to a show that made you feel more seen in its five-season run than you’ve ever felt before can be palpably painful. Thanks to both Issa Rae and Issa Dee for the friendship—it meant everything."
Insecure's finale was perfect because it was always about the messiness of love: "This speaks to the relationship between Insecure and its audience," says Bolu Babalola. "Even when storylines were controversial or considered frustrating, the show’s community hung in there, stuck with it, saw its heart, because they knew how much Insecure—and Issa Rae, the undeniable force and voice behind the show—loved its people, and trusted its intention to show Black people in all their glory and mess and humanity, their tragedy and their humor, their beauty. We saw each other in these characters, and it was more than seeing dark-skinned Black women desiring and being desired, failing and flying. It was that all the characters seemed not just a reflection, but real. Messy. They were more than a representation: A realization of known people, people who we could use as tools to know ourselves, to ask what we would do if we were in that situation, to reflect on what we love about ourselves. Insecure itself was a friend, and its–yes, messy–relationship with its audience was its own complex love story."
Insecure could be frustrating, but its finale was surprisingly satisfying: "The point Insecure’s final episode makes is that Issa never had to choose," says Nadira Goffe. "Even when it seemed like Issa’s actions were in service of her greediness, they weren’t. She didn’t have to choose between, she could choose in addition to, as long as she was honest about her choices and what she wanted out of them. I expected to be dissatisfied with the finale, perhaps because this season has been a tug-of-war between the values at the heart of the show and a drawn out pause to leave us lingering on the question of how it all ends. But honestly, I’m so tired of the narrative of the girl who doesn’t choose between the two men and instead melodramatically chooses herself. Why can’t she have both love and personal growth? Lasting friendships and a commitment to work, a career, in any form she wants it? Insecure says she can. She always could. She just had to believe she could make it work. And that, to me, is the greatest rabbit Insecure could ever pull out of the hat. Damn, am I gonna miss Tuesdays."
Logistically, everything makes sense in Insecure's series finale: "I suppose it’s fair the biggest complaint anyone will have after this finale is that it’s just not enough (even though the episode was 40 minutes long)," says Ashley Rae-Harris. "But, it’ll just never feel like we got enough time with these characters in this city. Issa Rae and the team behind Insecure crafted a world that’s difficult to leave. There was no perfect way to say goodbye, but 'Everything Gonna Be, Okay' comes close."
Jay Ellis recalls being terrified to play Lawrence: "People might think that Lawrence was easy for me to step into but it was actually the opposite," he says. "I was terrified to play Lawrence for a long time. Up to this point, everything I tested for, everything I had worked on was comedy, comedy, comedy. Man, I didn’t even know I could be vulnerable before Lawrence! I definitely feel like I got stretched, I found stuff I didn’t know was in there that I was able to bring to the work and the character. I feel like I’ve grown to be so much better, whether in my own preparation or listening when you’re in a scene with somebody and connecting. So much happens in the white space on a script, in between the lines, and I learned so much about really using that space to fully round out a character."
Issa Rae says she felt different making the final season: “I’ve literally grown as a person doing this show. I’ve grown in the industry and become more confident about my role in this industry,” she said. “I know who Issa Dee is. I know she’s grown from Season 1 to 5, in addition to my comedic voice.”
Rae says "hell, yes" Insecure's long development process was ultimately good for the show: "I realize how special my experience has been and how unique it is," she says. "And to the point of being on the right path, so many things have to go right, and so many of the right people have to be involved to make this show. Despite my frustration of being in development for such a long time, I think about the show that could’ve been and the show that is. And how much better the show is because of time and what it went through and what I went through. I already miss every part of this show and every part that went into making it happen and truly do feel grateful for the people who’ve been along for the ride. And who actually love these characters. I think if you love these characters, then you’ll feel satisfied by the finale. Hopefully. But, yeah, I’m just — I’m so happy that people are taking this show into their heart." Rae says the long development process "made me tap deeper into myself. In working with Larry Wilmore early on — that was for the workplace-comedy version of the show — being able to take that and what we discussed and tap into who I was at that time, that was a journey. And so much happened in my own life as I was developing the show, creatively and personally, that helped add to it. Everything happened the way it was supposed to with time." As a result, she says, "I feel secure. It’s so corny, but I do. Issa Dee has worn her heart on her sleeve in a way that has inspired me. This show has made me more openhearted and less closed off — though you’d have to talk to my friends about how true that is. But to me, it’s made me more vulnerable."