It's Finna Be Like Hella Over, Okay?!! Revisit Our 11 Favorite Insecure Episodes Before The Season 5 Premiere

By Keyaira Boone · Updated October 23, 2021

For four seasons, Insecure has given us stories about characters that worked hard, loved hard, and reminded us Trayvon Martin was somebody’s child and the FBI Killed Fred Hampton on their sweatshirts before laying their edges in the mirror.

The adventures of Issa, Molly, Lawrence, Daniel, Tiffany, Kelli, and the rest of the squad reflected the best and worst of what it means to be young Black and striving. They climbed mountains and combed through the messy together and along the way they guzzled cognac, embraced their sexuality, sought therapy, admitted their fears, designed their own dinner party fonts, shared finsta accounts, suffered sexual mishaps, and finally found a way to ask for what they wanted. 

For thirty minutes on HBO Sunday nights, the playful insults, shady debates, and undying loyalty of Black romance and sisterhood were put on full display. 

They woke up with missing tracks after a night of debauchery in the desert, reminded us to never send emails after recreational drug use, and kept it real about how things can change when your homegirl becomes a whole parent.

Insecure introduced us to new faces and celebrated a variety of Black art forms and acknowledged the way Black neighborhoods can be stripped of their identity.

The show took us to Inglewood, Malibu, Chicago, the Coachella valley, and the desperation lurking in Beyoncé’s DMs. It even anointed the entryway to The Dunes a cultural landmark that show-runner Prentice Penny compared to the Black Hollywood sign. 

As we gear up to see how our faves’ stories come to a close in the show’s final season, see 11 of our favorite Insecure episodes below.

01

We Can Thank Gina Prince-Bythewood For Our Sunday Night Laughs

Rae revealed that after spending high school studying theater, she was more interested in creating movies than serialized content. “I was super into film because of Love & Basketball specifically,” she said. “I wasn’t really thinking about TV because TV wasn’t really that poppin’ then. There just wasn’t enough representation then.”

02

“Broken as F*ck” – Season 1, Episode 8

“Seven writers over the last five seasons go on to get their own overall deals, we’ve seen six of our writers from these five seasons go on to become showrunners post-Insecure. We’ve hired and broken in two costume designers, a new DP (director of photography) to television.” “We tried to open as many doors as possible,” said Penny.

03

“Guilty as F*ck” – Season 1, Episode 6

It’s ironic but this episode about cheating shows some of the clearest depictions of Black love in the series. In a world of 28-acre birthday gifts and endless Birkin flexes, seeing a couple vocalize their intentions, ogle moderately priced engagement rings, and choose a couch with a layaway option felt super attainable.

04

“Hella Shook” – Season 2, Episode 5

Radical honesty is useful whether its coming from your sex buddy or your drunk auntie and this episode has both on deck. Also, it gives us shirtless Dro. We’re always here for shirtless Dro.

05

“Hella Perspective” – Season 2, Episode 8

This pivotal episode broke format by following several of the main characters over the course of 30 days that would change each of their lives forever. It also reminded us that you should probably stick to staycations when you’re sleeping on couches.

06

“Familiar Like” – Season 3, Episode 2

We love an adventure episode and this one reminded us of all the reasons clubbing fell out of fashion. It also took a realistic approach to housing challenges.

07

“High Like” – Season 3, Episode 5

This “Beyoncé-or-bust” mission combined our love of King Bey and protective styles with world-class sex and top-tier physical comedy. It also introduced us to Andrew, gave us a Bad Girls Club tribute, and let us get a glimpse of our boo Thug Yoda with his bool self.

08

Issa And Molly Were Not Always The Show’s Central Relationship

When Rae was writing outline after outline in development, it was in a meeting with producers that she began was talking about her real-life friendships and showed them a text from her homegirl. The response? “That’s the show.”

09

“Lowkey Thankful” – Season 4, Episode 3

This episode was all about setting boundaries and we were so here for it. Life’s too short to be letting mixed signals and mood killers steal our joy. We rejoiced when Issa’s brother reminded us we literally don’t have to do things that we don’t want to, and we were happy to see our girl Wendy Raquel Robinson (sketchy boyfriend, twins and all).

10

“Lowkey Movin’ On” – Season 4, Episode 10

Even when it’s painful, sometimes you just have to let a situation come to blows. And after a tidal wave of passive-aggression, it was nice to finally seee Issa and Molly’s drama wash over them in full force. The cameos were winners too. We love us some Aminé and some Alex Isley.

11

“Lowkey Happy” – Season 4, Episode 8

The set design, the color palette, the conversations, and the comedy all had us glued to the screen. Finally in the same place at the same time, Issa and Lawrence had a chance to be completely transparent about their relationship and bring out the best in each other again. But we didn’t appreciate how they clowned TSA Bae (he ain’t do nothing to nobody).