Good Guess, the second album of original songs from Brooklyn singer-songwriter Winston C.W., surveys the varied topography of human memory, finding hills and valleys in territory that feels both familiar and foreign. A song might arrive through rose-tinted glass, or as a self-critical reflection that casts the past in a single hue. But whatever the initial observation, it paves the way for more nuanced understanding, shedding light on previously overlooked intricacies of relationships both platonic and romantic—though, by the time all’s been said and sung, even these conclusions feel debatable.
This even-handed analysis is old hat for Cook-Wilson, who, as the frontman of New York sophisti-pop quartet Office Culture, detailed the highs and lows of city living on 2019’s A Life of Crime, an album full of characters finding joy and disappointment in equal measure in bars and backrooms. (Full disclosure: Cook-Wilson is also an occasional contributor to Pitchfork.) Good Guess localizes the drama, applying Cook-Wilson’s hyper-analytical introspection to the mind’s eye. With the hindsight that comes from months spent indoors, the haze of a previous life comes into focus, enabling more impartial evaluation of a time not so long ago that already feels distant.
Even with a clearer understanding of the past, doubt lies just beyond the frame. Uncertainty arrives in lockstep with each vignette, affecting every turn of phrase and chord progression. It oozes into the record’s central monologue, making for songwriting that’s rarely authoritative and keenly aware of its limitations, yet doing its best to describe things as they were. As Cook-Wilson sings on “Safety,” “That guilt will find you, no matter where you summer/No matter how long you hang your head.”
Offset by Cook-Wilson’s procession of muted piano chords, Carmen Rothwell’s bowed upright bass and Ryan Beckley’s hazy electric guitar heighten the miasmic, self-effacing verses of “Safety” and “Broken Drum.” Gradually, however, the players shift towards harmonic unison, and tense, dissonant performances eventually congeal into moments of warm melody. Simultaneously, Cook-Wilson’s songwriting becomes grounded and cogent, emerging from dazed ruminations with new wisdom on personal failings, whether it’s an awareness of life’s repetitive nature (“Broken Drum”) or an acknowledgment of how deeply the present is beholden to the past (“Safety”).
Beyond serving as backdrop for Good Guess’ ambiguous narration, this instrumentation propels the record’s most self-assured moments forward. The introductory instrumental of opener “Cakewalk” provides a sense of motion, its recollections of time spent with an ex-flame transitioning to a metaphor-laden exposition on the entire relationship as a meandering solo piano gives way to the full ensemble. Likewise, on “Birds,” the album’s most lighthearted tune, Cook-Wilson employs melodic vamps evocative of Randy Newman to playfully rib himself for his own past self-aggrandizing attitudes. It’s a spark of joy on an album that is otherwise serious and methodical in its approach to memory.
Experimental segues are abundant on Good Guess, but they sometimes feel isolated and nebulous. The instrumental “Swing Time” and its disparate, untethered instruments come off as indulgent, softening the momentum built over the record’s first four tracks. The winding lyricism and about-face turns from harmony towards a dirge-like procession on “No Regrets” are similarly contrarian, breaking from the album’s characteristic warm interplay. But in line with the record’s penchant for exploration, these suites are short-lived, as fleeting as the memories they soundtrack.
There’s no Rosebud in sight by the time Cook-Wilson arrives at the album’s titular conclusion, no final ruling as the mental evidence begins to pile up. “I look at your picture, squint ’til it bends/The eaves start rustling and I’m numb again,” he croons, encased by rumbling pianos and dissonant electric guitar, his vocals sounding spent as the album reaches its max volume before quickly fading to an outro of dampened pianos, quiet as it began. Nonetheless, it offers some closure; while the past remains unknowable, Good Guess illuminates the recesses of the psyche. There’s no real truth to be found back there, either—but eventually, you’ll have to turn around and come out.
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