October Monthly Rotation

October 2026 Playlist · Insecure 10-Year Anniversary

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

MONTHLY ROTATION 003

Hella Good Music

A soundtrack for figuring it out, making a mess, growing up, and becoming somebody you recognize.

Before Insecure gave us five seasons of Issa trying to figure out her life, it gave us a sound.

Music coming through car speakers on the way somewhere. A song underneath a night that was already becoming a bad idea. Something playing while friendships shifted, relationships broke open, careers changed, and Los Angeles kept moving around everybody.

The music never sat politely in the background.

It helped tell the story.

Sometimes a song knew what somebody was feeling before they did. Sometimes it made the mess feel better than it was. Sometimes it stayed with us long after the scene was over, until hearing those first few seconds could put us right back in an apartment, a car, a party, or a version of ourselves we had almost forgotten.

So October’s Monthly Rotation goes back to that feeling.

Not every song from Insecure. Not even close.

These are the ones that take us somewhere.

Thirty-five songs moving through the same strange territory adulthood does: trying to understand yourself, involving other people in that confusion, making questionable decisions, realizing the old life does not fit anymore, beginning again, losing things, finding things, and eventually looking around at a life you could not quite see from the beginning.

And because this is Insecure, growing up does not mean becoming serious all the time.

There is still a night out.

Still a song you know every word to.

Still something playing loudly enough to remind you who you were before you became whoever you are now.

October belongs to the music that followed us while we were becoming.

Thirty-five songs. Five chapters.

Play it in order. No shuffle.

Now Spinning

Press play before you continue, or let the music accompany your reading.

I. WHO AM I SUPPOSED TO BE?
The mirror-talk years. Confidence, uncertainty and trying on versions of yourself to see which one fits.

II. WELL, THAT GOT MESSY
Wanting people you shouldn't. Staying too long. Going out anyway. Everybody insisting they're handling it when absolutely nobody is.

III. MAYBE I'M GETTING SOMEWHERE
The job changes. The apartment changes. The plan changes. Uncertainty starts sounding a little less like failure and a little more like possibility.

IV. GROWING UP IS WEIRD
The quieter stretch. Love changes shape. Friendship changes shape. Sometimes you do too.

V. EVERYTHING GONNA BE, OKAY?!
Memory, home, old songs, old friends and the strange realization that somewhere along the way you actually built a life.

Liner Notes

Alright — Kendrick Lamar

There is a reason this is where the playlist begins.

Alright carries two truths at once: things are difficult, and we are still here.

That tension is part of what made it feel so at home in Insecure. The show rarely gave its characters the luxury of becoming one thing at a time. You could be uncertain and ambitious. Hurt and funny. Broke and still outside. Completely lost and somehow convinced you were going to figure it out.

Kendrick Lamar’s refrain does not erase what comes before it. That is precisely why it works.

“We gon’ be alright” means more when there has already been evidence suggesting otherwise.

As the first song in this collection, Alright is not a conclusion.

It is a dare.

Keep going.

We’ll see if it’s true.

Insecure — Jazmine Sullivan feat. Bryson Tiller

Eventually, figuring yourself out gets complicated by another person.

Or several.

That is where Insecure lives.

Jazmine Sullivan and Bryson Tiller trade suspicion, defensiveness, accusation, and desire until it becomes difficult to tell who is protecting themselves and who is making everything worse.

Which is, unfortunately, very on theme.

The song understands something the series understood especially well: insecurity does not always look timid.

Sometimes it argues.

Sometimes it accuses first.

Sometimes it checks a phone, withholds something, says too much, says nothing, or creates exactly the problem it was afraid of finding.

By the second movement of the playlist, everybody believes they are handling things.

This record arrives as evidence to the contrary.

Trouble on Central — Buddy

There comes a point when being dissatisfied starts becoming useful.

Trouble on Central sits inside that strange middle—the place where you know the current version of your life is not working, even if you have not figured out what replaces it.

That is an important kind of movement.

Not the cinematic breakthrough.

Not the montage where everything suddenly comes together.

Just the quieter realization that something has to change.

A different job.

A different neighborhood.

A different relationship to yourself.

Maybe a plan that sounds a little ridiculous until it starts working.

That is why the song belongs in the playlist’s third chapter, where uncertainty begins to shift from something happening to you into something you might actually be able to use.

Not there yet.

But moving.

WORLD WE CREATED — GIVĒON

By the fourth movement, everybody is quieter.

Not because life has become easier.

Because eventually you learn that volume cannot solve everything.

WORLD WE CREATED lives in the difficult space between what two people built together and what happens when that shared world can no longer hold them.

There is tenderness in that.

And grief.

Growing up sometimes means admitting that something can have been real without being permanent.

A friendship.

A relationship.

An apartment.

A version of yourself.

Some things deserve saving.

Some things deserve remembering.

Those are not always the same thing.

The playlist waits until nearly the end of this chapter to make that distinction.

Feels Good — Tony! Toni! Toné!

After all that becoming, there should still be a good song playing somewhere.

That matters.

Feels Good does not need to carry the emotional weight of everything that came before it. Its job is simpler.

Come outside.

Remember yourself.

Move something.

There is a particular pleasure in reaching adulthood and realizing that growth did not require surrendering joy. You can have responsibilities, history, heartbreak, bills, somebody’s birthday dinner next Saturday—and still know exactly what happens when the right song comes on.

That is why Feels Good belongs near the end.

Not because everything has been resolved.

Because everything does not have to be.

Sometimes adulthood is also realizing that joy does not require permission.

Turn it up. Insecure Anniversary Editorial

There may be no clean moment when we become the person we were trying to be.

Maybe there is only evidence.

An apartment that finally feels like yours.

A friendship that survived becoming different.

A decision you would not have known how to make five years ago.

A song you once heard while trying to figure your life out that now belongs to a life you actually recognize.

That may be why the music of Insecure stayed.

The songs did not simply accompany the characters.

They kept time with them.

And somewhere along the way, they kept time with us too.

You hear one now and remember the episode.

Then the apartment.

Then the year.

Then who you were when you first heard it.

Five seasons later, everybody had changed.

Ten years later, so have we.

The record is still playing.

About This Collection

Curated by
The Living Room Editor

Collection Title: Hella Good Music
Series: Monthly Rotation 003
Published: October 2026
Songs: 35
Time Period: 1990s–2020s
Genre: R&B • Hip-Hop • Rap • Neo-Soul • Alternative R&B • Funk • Soul
Listening Time: 1hr 30min

Collection Summary:
The soundtrack to The Living Room’s October issue and Insecure 10-Year Anniversary, Hella Good Music follows the sound of becoming across five seasons, thirty-five songs, and all the mess in between.

Arranged in five movements—Who Am I Supposed to Be?, Well, That Got Messy, Maybe I’m Getting Somewhere, Growing Up Is Weird, and Everything Gonna Be, Okay?!—the collection moves from uncertainty and questionable decisions through reinvention, heartbreak, adulthood, memory, and the strange realization that somewhere along the way, you built a life.

More than a collection of songs from a television series, these are records that helped Insecure tell us where its characters were before they always had the language to say it themselves—and, ten years later, still have a way of taking us back to who we were when we first heard them.

Play it in order. No shuffle.

Part of The Living Room’s Insecure 10-Year Anniversary Edition.
Read the Anniversary Edition →