Hella Good Music

A TLR Playlist for the Insecure 10-Year Anniversary

Five seasons. Thirty-five songs. One show that always knew what to play.

October 9, 2026

There are shows you remember by what happened.

And then there are shows you can hear.

Insecure knew the difference.

A song could arrive before anybody had figured out what they were feeling. It could follow Issa through Los Angeles, sit underneath a bad decision, make a night feel better than it was, or take over the credits while you were still sitting there thinking about what just happened.

The music never felt like something added after the fact. It belonged to the world of the show—the apartments, the drives, the parties, the quiet, the mess. It introduced us to songs we kept long after the episode ended and made songs we already knew belong to a different memory.

So for ten years of Insecure, we went back to the music.

Not every song. Not even close.

These are the ones that take us somewhere.

And because Insecure was always a story about becoming, this playlist is too. It starts with somebody trying to figure herself out. Then comes the mess. The mistakes. The people we love badly before we learn how to love them better. The strange middle where the life you had stops fitting before the next one has fully arrived.

And eventually, if you're lucky, you look around and realize you made a life.

Drop the needle.

Play it in order. No shuffle.

I. WHO AM I SUPPOSED TO BE?

Before Issa knew what she wanted, she knew how to talk to herself.

The beginning sounds like Los Angeles with somewhere to be and absolutely no idea what you're doing when you get there. There is confidence here. Some of it is real. Some of it is borrowed. Some of it only exists in front of a mirror.

01. Alright — Kendrick Lamar
02. No Small Talk — Kari Faux
03. Broken Pussy — Issa Rae
04. Palm Trees — GoldLink
05. Top Down — Kari Faux
06. Cheater For One — Issa Rae
07. Feel No Ways — Drake

Seven songs in and we're already making questionable decisions.

Sounds about right.

II. WELL, THAT GOT MESSY

Eventually, all that figuring-it-out starts involving other people.

People you want. People you shouldn't want. Friends who know too much. Relationships that don't end cleanly. Nights that seemed like a good idea several hours earlier.

This is the part where everybody thinks they're handling it.

They are not.

08. F.D.N. — Dreezy
09. Insecure — Jazmine Sullivan feat. Bryson Tiller
10. Quicksand — SZA
11. Crew — GoldLink feat. Brent Faiyaz & Shy Glizzy
12. Go Low — Issa Rae
13. ICY GRL — Saweetie
14. Gimmearide? — Kari Faux

No lessons yet.

We're still outside.

III. MAYBE I'M GETTING SOMEWHERE

Then something shifts.

The old job doesn't fit. The old apartment doesn't fit. Sometimes the old version of you doesn't fit either.

So you try something.

You quit. You move. You meet somebody. You get an idea. You decorate the apartment. You make a plan before you have any proof that the plan is going to work.

For the first time, uncertainty starts sounding less like failure and a little more like possibility.

15. Banana Clip — Miguel
16. Make It Out Alive — Nao feat. SiR
17. Summer Love — bLAck pARty
18. I Like That — Janelle Monáe
19. Trouble on Central — Buddy
20. The Glow — Victoria Monét
21. Bloct — Issa Rae

Not there yet.

But definitely not where we started.

IV. GROWING UP IS WEIRD

Nobody tells you that becoming more yourself doesn't necessarily make anything simpler.

Sometimes you finally get the thing you wanted and discover another problem waiting behind it. Sometimes the person you love can't come with you. Sometimes the friendship you thought was permanent changes shape. Sometimes you have to meet someone again after you've both had time to become different people.

The music gets quieter here because everybody finally does too.

22. Girl Blunt — Leikeli47
23. A BOY IS A GUN — Tyler, the Creator*
24. Case of the Ex (Whatcha Gonna Do) — Mýa
25. You Can't Save Me — SiR
26. Show You — Baby Rose feat. Q
27. Out of Your League — Blood Orange feat. Steve Lacy
28. WORLD WE CREATED — GIVĒON

Some things aren't meant to be fixed.

Some are.

Knowing the difference takes a while.

V. EVERYTHING GONNA BE, OKAY?!

And then, somehow, we're grown.

Not finished. Not suddenly in possession of all the answers. Just older. Softer in some places. Clearer in others.

So the last stretch gets to remember.

The songs you used to hear at parties. The songs that immediately put you back somewhere. The people who knew you before the career, the marriage, the baby, the business, the version of yourself you eventually grew into.

Insecure never needed adulthood to mean becoming serious all the time.

Neither does this playlist.

29. Blow the Whistle — Too $hort
30. Stanky Legg — GS Boyz
31. I Luv Your Girl — The-Dream feat. Jeezy
32. Still Ray — Raphael Saadiq
33. Glock Peaceful — Mereba
34. Feels Good — Tony! Toni! Toné!
35. For the Love of You, Pts. 1 & 2 — The Isley Brothers

We started with Alright.

Thirty-five songs later, maybe that's the whole story.

Not that everything worked out exactly the way anybody planned.

Just that somehow, after all of it—

we're alright.