Twelve Times Insecure Reached Peak Television Status

Like the rest of Black America, I am way too aware that this Sunday marks the end of an era and saying goodbye to Issa Rae and HBO’s Insecure won’t be as easy as we probably think. The cast and crew gave us five full, nuanced, awkward, complicated seasons to digest, showing us every aspect of Blackness in Los Angeles (which also served as a character and made the whole series a love note to the Southland, really), all through Rae’s character’s eyes. It was serious and silly, deep and shallow, filled with bad raps and great friendships, all inside of 44 30-minute episodes.

There were shows within the show (Looking for Latoya was my fave), supporting characters that stole every scene they were in (we see you Sequoia! Ahmal! Chad!), dark skinned (whatup Daniel) and light skinned (yeah, you aight Nathan… smh) romances, the best non profit name known to man (“We Got Y’all”), and folks we loved to hate (the variances on COVID have nothing on the variances of Condola’s name. Seriously). Insecure gave all of us a new appreciation for Bompton, Best Buy and banks. Every main character has left an indelible impression over those seasons, but if I’m being honest I’ll miss Rae the most. Her awkwardness was unmatched, and watching a character work through not always having it together felt like real life. Her rise to power player while doing what she does best, what she started out doing on YouTube all those years ago also feels like real life. Feels attainable. Feels real.

There will undoubtedly be a million tributes to the series as it wraps this weekend (and of course there should!), so I won’t keep going on and on about how important Insecure was to a generation that has specialized in making a way out of no way, while also not perfecting getting out of its own way. Instead I figured I’d just post a few clips from the series that highlight its brilliance, and also show how it changed the faces of (and on) television forever.

Cheers to Issa and the crew. You are appreciated.


This first clip is important because it set the tone for the entire series. In order to rock with Insecure you had to know that if there was one thing Issa Dee was gonna do, it was rap to (and hold conversations with) her mirror. It’s on the first page of the syllabus. And each “conversation” that was held didn’t disappoint. Roll the tape and reminisce on the love Issa had… for herself.

That compilation sets up what happened during the series pilot. Now that we’ve established that Issa will rap any and everywhere, it makes sense that she would take her talents to the stage to show the world her skills… even if it’s at the expense of her best friend, Molly. Ladies and gentlemen, do you remember where you were when you first head “Broken Pussy Rap?” Welp, here it is again. Enjoy?

Another major part of loving Insecure was understanding that the character Kelli was the hidden gem we knew we needed but never deserved. I could’ve swiped so many more videos from the Internet to show her contributions, but let this collection of clips from Season 1 serve as your Kelli Cliffs notes. Proceed with laughter.

Those first three clips showed the extremes the series would sometimes go to in order to showcase comedy. However, that was never the only thing Insecure was all about. There was balance, and a whole lotta cuss words, during the first season and in this scene we saw the potential range in both Rae’s Dee and Jay Ellis’ character Lawrence. “If the F word was a person” might be the best way to set up this clip. Whew.

On some shows there would be a breakup to makeup. There would be forgiveness (if not forget, um, ness) and the couple we were introduced to in the pilot would reunite until the next thing happened. Not here, which was refreshing and again felt real. Also I swear, if Tiffany and Derek’s parties were any more toxic, they’d be able to apply for government aid. Check the scene below from Rae and Ellis and see what happens when things fall apart like a Roots album title.

Yes, we all need a bit of a woosah after the heaviness of that scene. Thankfully we have Natasha Rothwell’s Kelli to the rescue. This clip, from when the ladies attended the BeyoncĂ© Coachella event during Season 3, is everything you need it to be. And I’m not saying that from a high horse. Nope. The ladies are high enough. Heh. It also gave us one of the greatest taglines in the history of television. You’ll know it when you hear it. I promise.

And then… the aftermath. El. Oh. El.

The first three seasons gave us the type of drama that comes from breakups and attempts at defining oneself, all within the confines of friendship and the ability to be vulnerable with those around you. However, what happens when that vulnerability becomes too much and basically drives a wedge between you and your person? Welp, bring on Season 4 and the beginning of what could’ve been the end of Issa and Molly as a duo. This scene, man. Lawd.

So… things weren’t good. Not even a little bit. However, after not seeing Lawrence for a long while, he was back on the scene, crispy and clean, with a new job and literal new lease on life. Then came the reconnection with Issa, who was still in the throes of her estrangement from Molly. A chance encounter led to this. Below. Click play. Please.

Wait… what you think? Insecure was going to make everything alright? You thought they would wrap up the season with celebratory raps and happy endings (not that kind… well, for Issa anyway. Heh)? Nah, that’s not how they play. Insecure is like a pitcher that throws curveballs to keep batters honest (um, I think we’re the batters. I didn’t really think that analogy through all the way but stay with me!) and make sure they have to guess what’s coming next. This clip below was definitely one of those curves. And if we’re being honest, Curveball was probably one of the names we used for the character never known as Condola.

Y’all good? I hope so, because as bleakly as Season 4 ended, Season 5 (the final season) gave us hope again. Hope for growth and dealing with situations and coming into oneself. These ten episodes skipped a few months and years and was a lowkey masterclass on maturing. I loved to see it. This clip below shows the ladies gathering one more time, being the (mature) foursome we grew to love.

Oh, wait. Yes I know I said there would be 12 scenes but honestly, keeping it at 11 makes more sense. The 12th and final scene will likely take place this weekend and rightfully so. Insecure has earned a chance to end on its own terms and give us what they want to give us. So, as we wait for the finale to air Sunday, feel free to insert your own favorite scenes in the comment section and express why you loved the series (I could add to let me know why you didn’t like it but I figure if that’s the case you wouldn’t be reading this anyway #ChadShrug).

It’s been a great run. Five seasons of peak Blackness. Five seasons of great television.

Issa classic.

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