Substack Summer Music Playlist! A Deep Dive into My Hand-Picked Songs for the Season…

Available on Spotify and Amazon Music

May 18, 2026

Summer is almost here, you know what that means? It’s time for me to unveil and unwrap my new Substack Summer Playlist! These hand-picked songs I’ve carefully curated for Summer are now available on both Amazon Music and Spotify

Each song was hand-picked for several reasons:

the emotional charge that comes with the changing seasons
lyrics that speak to my core and my current mood
the sunshine and feel-good vibes that come with Summer
and a few surprises along the way

So break out your earbuds, pop on these tunes, and let me know what you think of my Substack Summer Playlist — and share your go-to Summer songs in the comments!

BONUS TRACK: Before we begin, check out my collab with singer/songwriter Becca Roth, who turned my poem 6:04 Daydreams into an original song!

Okay, now we go back to regularly scheduled programming…

Substack Summer Playlist, The Deep Dive by Chris B. Writes

Song #1 – I Wish by Skee-Lo

I Wish feels like being young enough to say everything out loud. No filter, no polish, just truth with a beat behind it. It reminds me that summer used to be about wanting more and somehow being okay with not having it yet.

I Wish…

Song #2 – Hot In Herre by Nelly

Hot In Herre doesn’t ask you to think, it just makes you move! Windows down, volume up, no overthinking. It turns wherever you are into the moment to let loose in the summer heat.

Song #3 – Temperature by Sean Paul

Temperature lives in motion. It’s not meant for sitting still. It’s pulsating rhythm, pop reggae, and that feeling like the night isn’t going to end if you don’t let it.

Song #4 – Summertime by DJ Jazzy Jeff & The Fresh Prince

Summertime is the blueprint. The smell of sunscreen, the look of a fresh haircut, the sound of a basketball somewhere nearby… the kind of day that doesn’t ask anything from you. Just be there.

Song #5 – Summer Girls by LFO

Summer Girls doesn’t make perfect sense, and that’s the point. It’s messy, random, nostalgic in a way that feels like flipping through old memories that don’t line up but still feel right.

Song #6 – All Summer Long by Kid Rock

All Summer Long leans into the idea that summer is a story you keep retelling. A little exaggerated, a little blurred, but always worth going back to. It’s also a great mashup of Werewolves of London and Sweet Home Alabama!

Song #7 – Wild Night by John Mellencamp & Meshell Ndegeocello

Wild Night feels like stepping outside when the air finally cools. Not ready to go home yet. Not ready to call it a night.

Song #8 – A Bar Song (Tipsy) by Shaboozey

A Bar Song (Tipsy) is the modern version of losing track of time. It’s loud, it’s a little reckless, and it doesn’t ask permission. It just shows up and takes over.

Song #9 – In Too Deep by Sum 41

In Too Deep hits that early 2000s nerve—when everything felt bigger than it actually was. It reminds me how even the smallest things used to feel like everything.

Song #10 – AM Radio by Everclear

AM Radio feels like memory itself. Static, distortion, pieces of the past coming through just clear enough to recognize but not hold onto.

Song #11 – Blister In The Sun by Violent Femmes

Blister In The Sun carries an energy that doesn’t age. It’s awkward, wired, a little chaotic—in the way real life actually feels when you’re paying attention.

Song #12 – Wild Wild West by The Escape Club

Wild Wild West feels cinematic. Like driving somewhere with no real destination—just chasing whatever’s ahead.

Song #13 – Fresh Eyes by Andy Grammer

Fresh Eyes is a reminder that perspective changes everything. Same world, different light. Sometimes all it takes is slowing down enough to see it again.

Song #14 – Slow Day by Pinn HateBerry*

Slow Day is the exhale. The kind of track that gives you permission to not fill every second. To let the day be enough on its own.

*Thank you to my good friend Jeannie Ewing for this pick to add to my playlist!

Song #15 – Sunshine Song by mikey6strings

Sunshine Song feels like warmth you don’t have to earn. Just sitting in it. Letting it hit your face and not thinking about anything else for a minute.

Check out Erin Gregory Creative’s favorite artist mikey6strings y’all!

Song #16 – Heaven by Los Lonely Boys

Heaven feels like a quiet kind of hope. The kind that doesn’t shout—just stays with you long enough to believe things might actually work out.

Song #17 – Smooth by Santana & Rob Thomas

Smooth is summer at its peak. Heat rising off the pavement, everything moving a little slower, and somehow the moment stretching longer than it should.

Song #18 – Island In The Sun by Weezer

Island In The Sun feels like stepping away from everything that weighs too much. A reminder that peace doesn’t have to be complicated.

Song #19 – Toes by Zac Brown Band

Toes is about letting go of the schedule. Feet in the sand, nowhere to be, and finally being okay with that.

Song #20 – Island Song by Zac Brown Band

Island Song carries that same drift—like time loosens its grip a little and you stop trying to hold it so tight.

Song #21 – Banana Pancakes by Jack Johnson

Banana Pancakes feels like slowing the whole day down on purpose. Letting the world wait while you stay exactly where you are.

Song #22 – Cruise by Florida Georgia Line

Cruise is movement without pressure. Just going, not chasing anything, letting the road and the moment do the work.

Song #23 – Cool Down by Kolohe Kai

Cool Down feels like that shift in the air when the sun starts to drop. Everything softens. Everything breathes a little easier.

Song #24 – Island Style by Thunderstorm Artis & Iam Tongi

Island Style feels like community. Like music that isn’t just heard—it’s shared, carried, and lived in together.

Song #25 – (I Can’t Help) Falling In Love With You by UB40

(I Can’t Help) Falling In Love With You slows everything down. It reminds me that some feelings don’t need to be explained—they just exist.

Song #26 – Baby, I Love Your Way by Big Mountain

Baby, I Love Your Way feels like warmth at the end of the day. The kind you don’t want to rush past.

Song #27 – Boombastic by Shaggy

Boombastic brings the personality back in. It’s playful, confident, and doesn’t take itself too seriously—which is exactly why it works.

Song #28 – Fly by Sugar Ray

Fly feels like the late afternoon stretch. Sun still out, but you know it’s starting to fade. That in-between moment you wish would last longer.

Song #29 – Here Comes The Sun by The Beatles

Here Comes The Sun is simple in the best way. Light returning. A reminder that things shift, even when it doesn’t feel like they will.

Song #30 – The Joker by Steve Miller Band

The Joker leans into being exactly who you are. No explanation, no apology—just showing up as yourself and letting that be enough.

Song #31 – The Boys of Summer by The Ataris**

The Boys of Summer feels like the ending credits. The part where everything that just happened starts to settle in. Windows down, night air moving through, holding onto what you can before it slips into memory.

**Thank you once again to my music sister from another mister Mandy Franklin for contributing once again to my playlist, as is tradition! Amazing pick as always Mandy!