Nearly every aspect of Good Guess, the new album from Brooklyn-based Winston Cook-Wilson (who records solo albums under the abbreviated moniker Winston C.W.), seems oddly out of place, starting with the cover art. The sleek, clean design looks like it might hang on the wall of a Reagan-era yuppie stockbroker’s Manhattan apartment or possibly adorn the latest sampler from the 1980s new age label Windham Hill. The instrumentation is a somewhat anachronistic combination of piano, electric guitar, and upright bass. Cook-Wilson’s voice has a frail, innocent quality that seems to fly in the face of the song’s stylish art-pop. But whatever anomalies are contained within the album’s eight songs are, in the end, inconsequential. This is an exquisite album with a uniqueness that only adds to its charm and likeability.

As one-fourth of Office Culture, Cook-Wilson has been involved in some of the most tuneful, sardonic lounge-pop in recent memory, thanks to the albums I Did the Best I Could (2017) and A Life of Crime (2019). As a solo artist, Cook-Wilson’s albums Thirty (2017) and the mostly-covers Without a Sail (2020) see him paring down his sound to primarily vocals and keyboards but with the lyrical wit and musical sophistication intact. Good Guess could almost be seen as a compromise – adding musicians but stopping short of anything resembling a traditional pop/rock lineup.

For Good Guess, Cook-Wilson enlisted the aid of two members of the Brooklyn experimental trio Scree – Carmen Rothwell on upright bass and Ryan Beckley on electric guitar. With Cook-Wilson himself on piano, the result is a smooth, jazzy, artfully rendered take on singer/songwriter pop balladry. Comparisons to Donald Fagen, Joni Mitchell, or perhaps Warren Zevon are inevitable. It’s no coincidence that most of the album’s cultural touchstones are artists who flourished in decades past. The songs and their arrangements have a charming, retro quality but are original enough to wave off any accusations of stylistic laziness.

While Cook-Wilson is credited with writing seven of the eight songs himself (“Swing Time” is credited to all three musicians), the performances – recorded live in the studio over two days with no overdubs – are deeply rooted in improvisation. This allows the music to stay within the song’s themes of “trying to stay in the moment while feeling like you’re being held hostage by the past”, according to Cook-Wilson’s press notes. By allowing all three musicians to play off each other and “in the moment,” as it were – the performances are fresh and completely present.

Cook-Wilson’s complex chords kick off the opening track, “Cakewalk”, accompanied by twangy electric guitar figures and understated bass work. It’s a delicate, low-key affair, the melancholia occasionally broken by Cook-Wilson’s plaintive falsetto. The crossover jazz inclinations of Joni Mitchell are definitely in there, crossed with the moody folk of Nick Drake. “Business” combines the monotony of everyday life with ugly memories of the past: “After the morning broke like an ugly grin / I couldn’t feel anything but grief / Stole a quick glance through the pearly gates / Past a present I couldn’t leave / I had no business being there.”

There are moments here and there when the fractured piano-pop ventures into a more atonal, idiosyncratic territory, particularly on the striking “Broken Drum”. The piano and bass rumble atonally as Beckley’s guitar dances around in a jazzy manner that suggests Nels Cline or Marc Ribot. Likewise, the instrumental “Swing Time” has an experimental tilt that suggests an ethereal, new age approach to modern classical composition. The chugging syncopation of “Birds” – one of the more traditional sounding songs on the album – almost begs for the presence of a drum kit. Still, Rothwell’s insistent, tactile basslines provide all the necessary percussion (as does Cook-Wilson’s brief, playful solo, which almost sounds like it was executed on one of composer John Cage’s prepared pianos).

Good Guess closes with possibly the album’s most ambitious song – the title track. It’s by far the album’s longest song with a run time of eight minutes, beginning with Cook-Wilson’s lengthy piano intro, followed by his vocals accompanied by Rothwell’s scattered bass notes. Eventually, Beckley’s guitar crashes down in a swell of distortion, all slashing chords and sustained notes. Each section of the song enters the picture gradually and deliberately. Throughout the song’s slow build and eventual chaos, Cook-Wilson’s vocals remain calm and composed. “Remember me sometimes like you knew me when / It was a good guess lover, try again,” he sings as the song ends. The song, like the rest of this odd, gorgeous album, manages to artfully combine the idiosyncrasies of jazz and pop while all the while remaining tuneful, sophisticated, and quite irresistible.