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The 14 Best Episodes Of “Insecure,” Ranked From Good To Perfect

From Malibu to Coachella to everywhere in between, we got y’all.

Posted on October 8, 2018, at 3:51 p.m. ET

Anne Marie Fox / HBO

When Insecure first premiered, a lot of us didn’t know what to expect. Issa Rae had garnered audiences’ love and respect through her web series Awkward Black Girl and debut book of the same name, but would HBO allow her to keep things as authentic and black? After all, the network had never built a comedy around millennial black women. Thankfully, the answer was yes. Along with help from executive producer Larry Wilmore and co-creator Prentice Penny, Rae gave us the show we’d been waiting for, one that documents the humor, frustrations, joy, and heartbreak of being young and black right now. Three seasons later, the series is still at the top of its game. The episodes below represent the best moments Insecure has given us over the past three seasons: the ones that are so real we feel triggered and argue with one another all week on Twitter about; the ones that make us laugh every time we even think about them; and even the few that made us shed a thug (Yoda) tear. From Malibu to Coachella to everywhere in between, we got y’all.

Here’s the best of Insecure, ranked from good to perfect.

14. "Messy as Fuck" (Season 1, Episode 2)

HBO

Writer: Issa Rae
Director: Cecile Emeke

This episode makes the cut for one reason and one reason only — Thug Yoda (Tristen J. Winger). We're introduced to everyone's favorite neighborhood Blood when he runs into Lawrence (Jay R. Ellis), who is throwing out a Drake-themed card, his attempt to make up for dropping the ball on Issa's (Issa Rae) birthday. In the short but memorable exchange that earned him the nickname “Thug Yoda,” Winger hilariously goes from giving Lawrence relationship advice one moment to correcting his daughter on her use of words that begin with C because "This is a Blood house."

13. "Racist as Fuck" (Season 1, Episode 3)

Anne Marie Fox / HBO

Writer: Dayna Lynne North
Director: Melina Matsoukas

Insecure is never more fun than when all four of the girls are together, and we get our first taste of that in this episode when we’re introduced to Tiffany (Amanda Seales) and Kelli (Natasha Rothwell) for the first time at a house party. There’s shade, naughty one-liners, Divine Nine references, and black-ass debates. It was refreshing to see a group of young black professionals go from dick jokes to the importance of college degrees with ease. It was also clear in that moment that Kelli would become a breakout character unlike one we’d ever seen a black woman get to play.

Jared (Langston Kerman) also shines in this episode when it becomes clear that he’s a good catch for Molly (Yvonne Orji). He’s able to hold his ground as a blue-collar worker in front of her very judgmental friends with ease, while also showing her that he’s anything but intimidated by dating a boss-ass black woman. “I think it’s sexy,” he says, without breaking eye contact. And don’t get me started about the way he had Molly up against the car for that first kiss. Sure, the other shoe would drop later in the season, but it’s this episode that highlights why Jared is one of the best men to ever grace Insecure.

Also, honorable mention to this amazing line from Issa while dealing with microaggressions at work: “They’re having secret white meetings and they’re sending secret white emails.”

12. "Hella Great" (Season 2, Episode 1)

Justina Mintz / HBO

Writer: Issa Rae
Director: Melina Matsoukas

The appropriately titled “Hella Great” was probably the most highly anticipated of the three season premieres, because it followed the series’ biggest cliffhanger finale in Season 1 — the literal climax of Issa and Lawrence’s wild breakup. We had no idea how we’d find the two at the start of this episode; the writers even decided to do a trick fantasy date start to make it seem like they had reconciled. But when the face across the table fades from Lawrence’s to some random dude’s, we see Issa just wishing she were with Lawrence after a series of terrible first dates. The sequence breaks into Issa’s best freestyle on the show to date, “Cheater for One” —

I'm a liar, sweetie, I cheat on niggas, too (I do)
Probably shouldn't trust me or I'll hurt your feelings, boo
I don't wanna be here, but my ex won't take me back
So my broken ass is here, small-talking over apps
Put it down, girl, I'm so dead inside, nigga, I cry every day
You should get the check and here's the tip (check), run away

Amazing bars aside, this episode also contains a hilarious “wine down” party at Issa’s apartment where we meet her shady brother and get the return of Thug Yoda, who shows up with his fellow Bloods (that Blood walk!) and instantly falls for Kelli (“You bute and you thick!”). The whole thing is as deliciously chaotic as it sounds and results in a fire breaking out, because why not! And just when you think your heart can’t take any more stimulation, the closing scene is a quickie between Lawrence and Issa! It’s actually the last time the two have sex, but in the moment, you don’t know what’s in store in a season whose premiere packs that much punch.

11. "Hella Open" (Season 2, Episode 3)

Justina Mintz / HBO

Writer: Dayna Lynne North
Director: Marta Cunningham

“You’re a fuck nigga who thinks he’s a good dude” is one of the best reads ever given on this here series. It’s delivered by Tasha (Dominique Perry) to Lawrence after he ghosted from her family cookout to go hang out with his coworkers, and didn’t turn back up until it was over. The entire scene is really the only reason this episode made the list: It was a true turning point for Lawrence, who up to this point had been the victim of betrayal and was real comfortable on that high horse until Tasha knocked him right on down to earth. Their short love affair was a necessary example of the danger of rebound situationships. Lawrence went running to the one woman he knew for sure would give it up, so that she could lick the wounds Issa’s cheating caused. The problem is, he knew Tasha had real feelings for him, and what transpired in the first three episodes of the season is a cautionary tale about what happens when you take advantage of someone's feelings and allow them to be collateral damage in a messy breakup.

10. “Shady as Fuck” (Season 1, Episode 5)

HBO

Writer: Ben Dougan
Director: Melina Matsoukas

Neither Insecure nor its fanbase were ever the same after this episode. It’s the moment the series proved just how far it was willing to go. It’s the plot point whose repercussions the characters are all still affected by in one way or another. It’s when Issa cheated on Lawrence by having sex with Daniel in the music studio. A black woman cheating on her faithful boyfriend is a kind of offense we rarely get to see on TV. The last similar betrayal on a black show that comes to mind is when Maya cheated on Darnell in Girlfriends back in the early 2000s. And the fact that they juxtaposed it with Lawrence turning down an advance from Tasha in the very same episode only made it worse. What’s almost more interesting than what happened onscreen is what happened online: Issa was clearly in the wrong, but a lot of women understood why she did what she did. Men rationalize cheating all the time but to see women do it had a lot of men shook. The #LawrenceHive was born by the end of the night. And in the words of Drake, nothing was the same.

9. "Real as Fuck" (Season 1, Episode 7)

HBO

Writer: Prentice Penny
Director: Kevin Bray

Seeing Daniel (Y'lan Noel) and Lawrence standing next to each other is truly one of the most terrifying frames in Insecure history, especially because their first run-in ever happens before Lawrence knows Issa cheated on him with Daniel a mere two episodes before. It’s something Issa and Molly desperately try to avoid when Daniel shows up to Issa’s WORK party to confront her about ignoring him since they had sex. But fate is fate, and by the end of the episode, Issa finally has to come clean to Lawrence. The hurt and anger in Lawrence’s response makes it one of the most devastating scenes of the series.

This is also the episode that features Issa and Molly’s worst fight. The besties exchange verbal blows about their love lives when Molly gets defensive about Issa suggesting she see a therapist. Molly’s whole aversion to therapy highlighted a common mindset in the black community and opened the door for an important mental health conversation. The plotline ends with Molly getting a (much-needed) therapist at the start of Season 2.

8. "Ghost-Like" (Season 3, Episode 8)

Merie W. Wallace / HBO

Writers: Issa Rae, Natasha Rothwell
Director: Regina King

The fact that this show found a way to put the ladies in a literal graveyard where their exes keep popping up like the ghosts they are is why Insecure is so fun. It’s Issa’s birthday and Molly and Kelli take her to an outdoor movie screening — located in a graveyard — of the blassic The Last Dragon to celebrate. Lawrence pops up. Jared (whom we hadn’t seen since Season 1!) pops up. Kelli’s ex Quantrel (whom we’d never met before because Kelli switches men like underwear) pops up! Ghosts are everywhere! The most gratifying of these run-ins is Molly’s with Jared, whom Molly ended things with after he shared that he had hooked up with a man once when he was younger. In Molly’s mind, that meant he was gay, and because she couldn’t get past that, she gave up a good man. When Molly sees Jared at the event with another man, she jumps to the conclusion that she was right all along and that he is in fact gay. But when they run into each other again while leaving the screening, it’s revealed that the man is actually Jared’s brother, and they’re both there on a double date with their beautiful black girlfriends. You can practically see the egg running down Molly’s face as she’s introduced to the woman who was wise enough not to let Jared get away. It’s an amazing payoff that showed that Insecure writers really do have some long-term plotlines in place. Another example of that planning: Issa ending the episode alone on her own couch. Season 1 ended with her on the couch crying in Molly’s lap; Season 2 had her going to Daniel to sleep on his couch after moving out of her and Lawrence’s apartment; and Season 3’s ending showed her growth — that she was finally independent and OK being alone.

7. "Fresh-Like" (Season 3, Episode 4)

Merie W. Wallace / HBO

Writer: Dayna Lynne North
Director: Stella Meghie

Usually it’s the episodes that have everyone in them that are the strongest, but “Fresh-Like” is perhaps the best showcase of Issa’s storyline removed from her friends. The majority of the story centers on Issa and Nathan spending the day together in what turns into the cutest date to ever happen on the show. They tour some of what Issa considers “the real LA,” and get to know each other playing a game of Truth or Dare that ends with them skinny-dipping in the pool of the house Issa grew up in as a child. Despite the naked sprint that takes place to avoid getting arrested when the current tenants come home, the date is pretty perfect. It even ends with tacos and a top-notch first kiss. Some of the best dates are the ones that you never want to end, and that’s how Issa, Nathan, and all of us at home watching felt about this one.

6. "Hella Disrespectful" (Season 2, Episode 7)

Justina Mintz / HBO

Writer: Prentice Penny
Director: Kevin Bray

Everyone is trippin’ in this episode — hence its title. Issa goes from trippin’ over her oral-sex-gone-wrong moment with Daniel to trippin’ over Lawrence bringing a date to Derek’s birthday dinner (only one of these is justified). Lawrence is trippin’ for bringing Aparna (Jasmine Kaur) in the first place instead of just rescheduling their plans like he intended to. Molly is trippin’ over Dro (Sarunas J. Jackson) bringing his wife Candice (Gabrielle Dennis) to the dinner party (nothing about this is justified). Dro is trippin’ by having sex with Molly in the restaurant bathroom to get her to stop trippin’ about Candice being there. (I don’t care if their marriage is open — you came with your wife! She’s right there in the building!)

All of this disrespect comes to a head when Issa storms out of the dinner and Lawrence goes after her. It’s the first time the two have seen each other since they had ex-sex in the Season 2 premiere, and all the built-up hurt and resentment reach a boiling point, leading to their biggest fight to date:

“Was it worth all that time I spent supporting your depressed ass?”

“Probably not as much time as you spent being a fucking hoe.”

In the words of Nene Leakes, “Whew, chile. The ghetto.”

5. "Obsessed-Like" (Season 3, Episode 7)

Merie W. Wallace / HBO

Writer: Prentice Penny
Director: Kevin Bray

“Obsessed-Like” is a flawless showcase of what this show is best at creating — relatable content. The concept of ghosting has existed for longer than we had a term for it, but it seemed to peak in popularity once given the clever title by millennials. It wasn’t clear until this episode — when Issa realizes that Nathan ghosted her — that it would be one of Season 3’s biggest themes. The entire episode is a hilarious account of all the steps one goes through after being ghosted: the period of denial when you think they still might call, posting a thirst trap online to try to get their attention, stalking their social media pages for clues, stalking them IRL (this is where we get into the danger zone), accepting what has happened, blocking them, and, of course, the most harmful of them all, rebounding with someone familiar (like an ex) for attention. The whole thing was so triggering: It was like a giant look in the mirror at one of life’s worst feelings. The icing on the cake was the brilliant idea to give a literal voice to Issa’s inner thoughts, making the whole thing twice as funny. And the scene in which Issa (in her pajamas and a trench coat) and Molly show up to Nathan’s house — under the guise of Molly wanting to see his roommate Andrew, whom she’d gone on a date with — is one of the funniest moments in the show’s history. His laptop password is absolutely not your name, sis!

4. "Broken as Fuck" (Season 1, Episode 8)

HBO

Writer: Issa Rae
Director: Melina Matsoukas

“MALIBUUUU!” is why I knew the movie Girls Trip would be so successful. The pure entertainment that is four friends on a vacation together never gets old, especially when those four friends are black women, because we rarely get to see that onscreen. Every moment in this episode, from the night out at the club to the fight in the hot tub, is pure comedy. Kelli especially shines with her nonstop flow of funny one-liners, half of which I’m sure Rothwell improvised. I mean, just the exchange between her and Issa — “Do you ever listen to yourself?” “All the time, I have a podcast” — makes this episode deserve a spot in the top five.

But it’s far from a girls-only episode, as Lawrence and Issa finally exchange some messages for the first time since he discovered she cheated. The last few scenes set us (and Issa) up to think that Lawrence is ready to try to forgive her and repair the relationship. She leaves the Malibu trip early to meet him at their apartment. The cameras show them walking in separately, using the characters outside the apartment complex as a subtle clue that significant time has passed from when Lawrence gets there to when Issa arrives. When she walks in, she sees his keys on the counter and smiles, thinking he’s in the bedroom — but instead she finds all his things are gone EXCEPT his Best Buy uniform shirt, symbolic of the job he settled for in an attempt to prove to her that he was making an effort to move past his unemployment and subsequent depression for the sake of their relationship. The scene then cuts to Lawrence, in Tasha’s bedroom, where he’s — excuse my French, there’s no other way to put this — fucking the shit out of her. Lawrence’s whole lil’ revenge moment was so cold that people kept tweeting about it until the Season 2 premiere a year later. He even took the pillow on his side of their bed! The #LawrenceHive has never had a bigger win.

3. "Hella Perspective" (Season 2, Episode 8)

Justina Mintz / HBO

Writer: Issa Rae
Director: Melina Matsoukas

If the Season 1 finale is an example of a messy way to end a relationship, the Season 2 finale shows how to do it right. It takes Issa and Lawrence an entire season to unravel and heal from their relationship’s tumultuous ending, but the payoff is a beautifully humane scene of the two of them having a healthy discussion about what went wrong. To quote, well, myself:

“In the scene, the two sit in the kitchen of the empty apartment they once shared, for the very last time before handing in their keys, to have ‘the closure talk’ that every breakup deserves but doesn’t always get. Lawrence apologizes for shutting down when his professional plans didn’t shape up and he couldn’t provide for them the way he wanted to. Issa apologizes for not knowing how to be there for him during his depression. And then she addresses the elephant in the room, the ultimate cause of their demise — her cheating on him with her ex-boyfriend. It was in that moment that she says the words that broke me, Lawrence, and probably anyone who has ever betrayed or been betrayed by someone they loved: ‘I wish I could somehow convince you that it wasn’t about you. You’ve only ever loved me and expected me to want the best for you and I promise I did.’”

2. "Hella LA" (Season 2, Episode 4)

Justina Mintz / HBO

Writer: Laura Kittrell
Director: Prentice Penny

There are so many goodies in the gem of an episode that is “Hella LA” that it’s hard to do the entire thing justice. Issa, Molly, and Kelli go to a day party called “Kiss & Grind,” and so much foolishness ensues as Syd from the R&B group The Internet spins the playlist of our dreams in her cameo as a DJ. Issa decides to meet up with a guy she met on Tinder at the party, only to get publicly rejected because she “looks different in real life.” She also runs into Daniel for the first time since she told him he was “an itch [she] needed to scratch” last season, so...an awkward reunion. On the other side of the party’s huge indoor/outdoor venue, Molly finds out her childhood friend Dro is in an open marriage after things get a little steamy between them while dancing to “Slow Motion” by Juvenile (relatable). Shell-shocked, she has to decide if she’s willing to get involved in that type of situation, opening the door to yet another regrettable decision. Meanwhile, Kelli spends the party, as she puts it, “catching!” and talks them into meeting up with one of her new prospects at a diner after the party. It is there that he and Kelli fail to be discreet as he fingers her under the table surrounded by all their friends (bruh!) — including Issa, who flees across the restaurant to Daniel’s table in shock. They laugh about it and silently decide to sweep their drama under the rug, opening up yet another Pandora’s box.

Across town, Lawrence actually manages to match the shock value of Kelli’s dalliance when he finds himself in a threesome with two nonblack women he met at the grocery store. In an interesting turn of events, the threesome goes from too good to be true (in his mind) to a disaster when he comes before the second girl gets her turn with him. Things go from awkward to bad real quick when the women berate him for not being able to get hard instantly like the other black men they’ve done this with (it’s clearly a fetish of theirs). “What’s the problem? We’ve been with a bunch of other black guys who can come and keep going,” one says, annoyed. “You know who really could fuck? LaMarcus,” says the other before they get off the bed, do some coke, and make plans for what to do with the rest of their night as if Lawrence is not right there. The entire ordeal goes to show that sometimes sex fantasies should remain just that. By the end of the episode, Lawrence is outside his old apartment, the one he shared with Issa, silently questioning if the grass is truly greener on the other side.

1. "High-Like" (Season 3, Episode 5)

Merie W. Wallace / HBO

Writer: Regina Y. Hicks
Director: Millicent Shelton

The only person who can top Kelli is Kelli, which is the only reason “High-Like” managed to beat “Hella LA” for best Insecure episode. It has all the winning elements we’ve grown to love seeing on the show — all the girls, a road trip, cute men, a hilarious fight — and some new ones. The girls go to Coachella, or Beychella as it is now known, to see Queen Bey and have their last group turn-up before Tiffany has her baby. Issa takes them on a hoe-mission to meet up with Nathan and his friends at a “black people pool party” before going to the festival. There they all take Molly (“I’m Molly squared,” Molly jokes once the high hits) and what happens as they head to Coachella can only be described as Emmyworthy content.

Issa and Nathan wander to a Ferris wheel high and, when it gets stuck, have one of the most electric sex scenes Insecure has ever given us. Down below, Kelli, Molly, and Nathan’s homeboys end up having to “battle the whites in the field” after a white woman blocks Kelli’s view of the stage by mounting her friend’s shoulders. The group gets kicked out for fighting right as Beyoncé is about to take the stage. In a desperate last-minute attempt to see Bey, Kelli risks it all trying to bum-rush the gate, only to get Tasered by a security guard. She falls facedown to the ground, pees on herself, and, as her friends run to her, cries out, “Remember me different!”

The magic of Insecure is that the show managed to take what should’ve been a triggering moment for black women and turn it into the most hilarious sequence of the series to date. When Issa finds them back at their rental house, everyone has reached the “I don’t want to be high anymore” portion of the drug trip: Molly is trying and failing to do work, Kelli is mad at everyone because of what she calls “tase rage,” and Tiffany is in the closet crying on the phone with Derek because she had a piece of an edible while pregnant. If the episode had ended there it still would’ve been at the top of this list, but just when you think it cannot get any wilder, Issa goes to the convenience store the next morning and runs into Lawrence — whom we had not seen all season and were made to believe was gone from the show for good. Whew, AN EPISODE!

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