Through pining comes purpose. Paul Cherewick, monikered Paul Cherry, makes a departure from pining for an unrequited love on his debut LP Flavour toward the hunger for creative fulfillment on Back on the Music. “Bouncing off the bottom: this pattern is the problem…” is the melancholic opening line of the new album, a meandering meditation on the life of an artist: chasing inspiration, finding community, and the struggle to maintain both. Throughout the buoyant, alright-on-the-outside tracks that make up his second album, Cherry staggers and stumbles back into love with his life and craft.

Music becomes personified inside Tootsie Roll, becoming an ugly, grinning trench coated villain plucked right out of a vintage Max Fleischer cartoon, cooing to the listener, “You know you want me. Take me, take me,” harmonizing over his own voice. Almost as if through excess, inhibition and precise self-analysis, Paul Cherry may find quiet. In the luxuriant arrangement of the title track, Back on the Music he sings, “You love to play, but it don’t pay. Feels like you’re caught in check mate.” Not everything fits neatly within the lines of these songs, as in the lonely, wobbling flute melody that carries us out of It Happens All the Time. Cherry shows us that often the path back to one’s self— disguised in this album as “Music”—is a wavering one.

Cherry began his musical journey in a small suburb of Detroit, playing banjo and guitar into his teenage years. His love for making music brought him to Chicago, where he studied classical composition at university. It wasn’t until winter of 2015 when, holed up in his apartment, a converted storefront space without windows in the heart of Chicago’s Humboldt Park, that the Paul Cherry sound emerged. Focused sharply on teaching himself the piano, playing through the jazz standards of The Real Book, jazz chords and melodies laid the foundation of Cherry’s signature sound as evidenced on the Flavour LP, at times cross referencing more modern takes on pop jazz from Michael Franks, Paul McCartney, Jeff Lorber, and Donald Fagen.

Paul Cherry’s music evokes a love for sunny ‘70s and ‘80s grooves. Buried beneath cynicism and introspection is a winking optimism. The juxtapositions of Cherry’s warm instrumentation and the apathetic lyrics on More Fun are an exercise in subversion. “I’m so ready to have more fun with my life,” Cherry sings over a syncopated bassline, performed by bassist and collaborator Joseph Faught, convinces us that he’s more than ready. He’s made it.