Dig deep enough into Paul Cherry’s debut album Flavour, past the breezy yacht rock melodies, the jazzy flourishes, and the solo-era Paul McCartney eccentricities, and it’s clear the Chicago pop whiz spends a lot of time on his phone. Though he’s not totally a hyper-online social media addict, the LP’s 10 songs often deal with the headaches and heartbreaks that come with how we fail to communicate through texts and tweets. Take the telephone ringing that opens the album, the voicemail skits, or the lead single “Like Yesterday,” on which the 26-year-old musician sings, “Looking through my phone / Messages that I know I shouldn't send / Already sent.” Where the album’s charms are obvious in Cherry’s charismatic vocal deliveries and his ear for decadently silky ‘70s-inspired arrangements, it’s his anxiety that gives Flavour its heart.

Flavour, which is streaming in full below, marks the culmination of Cherry finally figuring out his sound, a process plagued by his own self-doubt and insecurities. He tells Noisey, “For a long time, I wasn't taking music super seriously. My goal was just be around town as a ‘local musician guy.’” Already a mainstay around Chicago’s DIY shows, his earliest offering, 2014’s self-recorded On Top EP found him dipping his toes in scuzzy garage rock along with sleepy, laid-back guitar pop. While it had its charms it was clear he approached his craft with some ironic distance. After all this is a guy who would goof around on Twitter making fake jingles for Olive Garden, Cherry explains, “I didn't know how to record or what to do with my own music. This was just me making music for fun.”

The EP caught the ear of local label Feeltrip co-founder David Beltran, who promptly put it out on tape. Cherry says, “Even though I was just fucking around, having someone believe in what I was doing was proof to myself that I could make pop music.” His newfound confidence led to taking recording and writing seriously and he started working with his friend and future Polyvinyl-signee Anna Burch on her first album. “Those songs were the first things I ever worked on that weren’t my own. The more I learned about recording, the more I got addicted to hearing those tracks we made and seeing how they hold up.”

Working behind-the-scenes on Burch’s album and on songs by the late Chicago musician Trey Gruber’s Parent songs gave him the inspiration to finally focus on himself. “I was watching my friends in Mild High Club and it was so clear that they had it. And it was unclear to me what " it" was. Why do some artist have this magnetic, incredible thing about them and others don't? Anna Burch has it. Trey Gruber had it,” he explains. He adds, “My friends were also just working really hard at their craft and that’s what I had to do. As soon as I realized that, I started pumping out jams that I thought were cool. It took me over a quarter of a century to get to a point where I like my own music.”

Cherry is right: there is a lot to love on Flavour. Tracks like “So Easy,” which was originally released in 2014 on a split with Chicago garage-pop lifers The Lemons, is revamped, scrapping the original’s lo-fi sensibility in favor of immaculate production and daydream-inducing guitars. Comparing those two versions is a perfect representation of how Cherry stepped up his game. Same goes for the piano-led “Changing Times,” which was written the day Trump got elected. While not an outright protest song, he decries that “nobody’s putting all their words in a song / they’ll just bicker and fight / and argue in spite / all day long” over wistful flute-led orchestration. It’s simple but it’s also affecting number even without knowing its political resonance.

Other songs like opener “Hello Again” add melancholic horns to highlight the way Cherry yearningly croons, “I’ve found a friend / finally someone to fit with me.” He explains, “The whole album is basically dealing with different ways we experience missed connections. The opener ‘Hello Again,’ which is basically like a ‘get-you-know-you’ snippet song, is about finding a friend online when you’re feeling lonely.” The ways Cherry magnifies the quiet sadness that can come with spending too much time on your phone.

There’s no better example of this than the album’s best track “I See U.” It’s a distinctly 21st century break-up anthem about checking in on your ex’s Facebook. He sings, “And I see you / when I open my eyes / tears hit the screen on my phone as I swipe / I’ll delete you when the timing is right / But I still need a clear picture of you / to sleep at night.” But more than being a bittersweet farewell for the social media age, it’s the best encapsulation of Cherry’s musical ambitions. The song boasts an indelible hook, mesmerizing horn solos, and a bridge that somehow sounds straight out of Ram without being McCartney pastiche. When I mention that to Cherry he says his parents named him after the former Beatle, saying with a wink, “I’m just investigating music and trying to make something I love from the albums I already love.”

Josh Terry is a writer in Chicago. Follow him on Twitter.

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