Happy & Sad: 31 Bittersweet Bops For Summer's End Pop songs that illuminate the shades of change

Enlarge this image toggle caption Emily Bogle/NPR Emily Bogle/NPR

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Denim jackets adorned with cutesy enamel pins have slowly returned to outdoor patio hangs. Neighborhood pools have closed. Hot Girl Summer has transitioned to Hot Girl Semester. Daylight still creeps into night, but dusk feels a little quieter, cooler. The summer's coming to an end.

When I asked Twitter what theme should close out the third season of roséwave — NPR Music's sommelier-level summer playlist series — y'all must've been in your feels, because "bittersweet summer's end" narrowly beat out "froséwave," meaning I'm just gonna have to save that trashy pop playlist for next year.

But like a pink ombré hair dye, some of the best pop songs illuminate the shades of change — whether they are seasonal, emotional, romantic or the big questions of life. Kacey Musgraves, ever the roséwave inspiration, immediately comes to mind with her song "Happy & Sad": "I'm the kind of person who starts getting kinda nervous / When I'm having the time of my life."

Happy & Sad is about finding the nuance in sad songs that sound happy, happy songs that sound sad and songs that fall somewhere in-between. There's nostalgia for endless summers in Chance the Rapper's "Do You Remember," but as Ben Gibbard's wistful hook reminds us: You really have to hold onto that feeling. Tyson Motsenbocker's richly textured ballad "The Last Summer" beautifully illustrates the tinge of sadness that accompanies life's gradual distortions: "We made plans for the world / Thinking we'd stay the same / Burn like Moses' bush / Where the leaves don't change." HAIM's "Summer Girl" walks on the wild side with a California breeze, but Danielle Haim wrote it to be the sunshine for her partner, to be "his summer when he was feeling dark."

And then there are the breakups that throw us off course or set new ones, heard in Rilo Kiley's throwback '60s-pop confection "Silver Lining," Baby Rose's defiant "Show You," The 1975's gauzily downcast "Somebody Else" and "Missing U" by Robyn, a pop singer who knows a thing or two about songs that live inside and burst out of heartache.

But Happy & Sad is not all bleak. After all, what is change but an opportunity or at least an acknowledgement that the future's unwritten? Or, as Sheryl Crow nonchalantly put it, "She wanted to know if I could tell the future / I said, 'I've never been there before, but the brochure looks nice.'" (Thanks to the L.A. Times' lovely profile, I now know that Prince covered "Everyday is a Winding Road" in all of his Purple One-ness.) The playlist closes with Des'ree's "You Gotta Be," an empowering '90s hit that challenges what the future holds; that hug for a hook ripples through every season: "You gotta be bad, you gotta be bold, you gotta be wiser."

Thanks to roséwave contributors who shared songs for the playlist, including Sidney Madden and Marissa Lorusso.