Rising stars and classic roots: must-listen Chicago jazz musicians.

artwork by Wyatt Warren.


“Jazz” as a name is somewhat of a misnomer, an agglomeration of genres and locations, histories and roots: the islands of the Caribbean, the floodplains of Mississippi, the gabled streets of New Orleans. But like the name, these roots converged in Chicago. 

The Chicago jazz scene is not what it once was. But that is not a bad thing. The modern scene is diverse and liquid. New voices merge with old ones. New forms are tested. Old forms are revived. Here are some standouts from modern Chicago jazz:


1. The Avant-Garde Veteran: Henry Threadgill

Henry Threadgill is no stranger to the Chicago jazz world: he was born, raised, and studied in the city’s scene. But he is no traditionalist. A multi-instrumentalist on saxophone and flute, Threadgill has made waves through his use of avant-garde techniques and “free-jazz” stylings. Threadgill’s unique instrumentation, strong dissonance, and confusing melodies have redefined the world of alternative jazz. There’s something strangely familiar about his music: when listening, one can hear the recognizable forms that should be there, but they are instead stripped away to create something haunting, confounding, and raw. Keep an eye out for his odd song titles as well.

Must-listen: 

1988’s Easily Slip Into Another World is, as the title suggests, a perfect introduction to Threadgill’s strange musical mind. The opening track “I Can’t Wait Till I Get Home” appears innocuous at first, but the song’s screaming saxophone solo gives a glimpse of what’s to come. The album’s avant-garde highlight comes at the seven-minute long “Let Me Look Down Your Throat or Say Ah,” a slinking track complete with dissonant violins, clarinets, and a slow minor-key descent into madness. Closing off the 46-minute album is the drum-heavy, high-energy “Award the Squadtett,” which feels very much like one is getting chased by a swarm of cartoon-ish bees.

2. The Fusionist: Mai Sugimoto

Another Chicago native, Mai Sugimoto sits amid a prominent scene of Asian-American jazz musicians, bolstered by events such as the Asian American Jazz Festival. What sets her apart is her ingenuity and her prowess for improvisation and composition. Her musical stylings are uniquely rooted in the city, but also extend to Sugimoto’s Japanese heritage and modern experience. On her debut Born/Raised, she juxtaposed Japanese children’s songs with more familiar American musical stylings. Her work with quartet Hanami similarly attempts at rendering her cultural background, in this case through the keys of a saxophone. Recently, however, Sugimoto’s music has been reactive: first to the pandemic, then to an epidemic of Asian-American hate crimes. Her dry, witty playing and minimalist compositional style invite one to react to what Sugimoto has been asking all her life: Who am I? What place do I have in this world?

Must-listen:

Sugimoto’s most recent piece, 2020’s monologue, has a type of introspection not seen in her earlier work. It is stripped down and clean. Recorded in the Loop amidst the pandemic, the city sounds and gritty isolationism bleed through each track. The nine-minute eponymous opener is shrill yet quiet. Sugimoto improvises over silence, creating a strange musical journey akin to Threadgill’s fantastical worlds. “Ab,” the album’s shortest track, is a slow, flute-heavy haunt. So is the grating “hysteria,” another interlude that defines the album’s visceral, intense reaction to a world in chaos. “migratory season” takes a more sultry approach: the saxophones are deep, almost sweet. The closer “corridor” brings in soft drums and lilted arpeggios as the album comes to a noisy, sour end.

3. The Jazz Age Belle: Roya Naldi

Perhaps the city of Chicago reached its zenith during the 1920s. The age of flamboyance, of jazz and theater, of murder and mystery — a city at its height. But perhaps this is all a romanticization, a farce. Roya Naldi seems to believe the former. The Chicago-born artist, in all aspects — music, fashion, and life — works to keep this era alive in her music. And work she does. Her honey-sweet voice croons over jazz standards, forgotten classics, and original compositions. Her band follows closely, weaving rich tapestries of rhythm and trumpetry. It may be time to break out the flapper-skirts and do the Charleston once again; although Naldi still manages to infuse modern sensibilities into her nostalgic work.

Must-listen:

2020’s A Night in June is currently Naldi’s only full-length album, but it neatly ties together eras of jazz, soul, and traditional pop into a listening experience perfect for a romantic dinner, a Lady and the Tramp movie night, or even a late night drive in your Ford Model T. “Crying Myself to Sleep” takes stylistic inspiration from Lady Ella herself: it is sweet, soulful, and smooth as butter. Naldi’s voice and band weave together wistful melodies and sultry rhythms. “Sweet Child” stays true to her 1920s roots — it is a foot-stomping, traditionalist work. “Blue Thoughts” brings on piano virtuoso Paul Asaro for a quiet, candlelight contemplation that never tires. Finale “Sentimental Gentleman from Georgia” is a lively improvisational work, with colorful saxophone solos, funky rhythms, and experimental lyrics that one could only ever find at the mansion of Jay Gatsby himself.

4. Local Rising Star: Sylvia Christine

While not a “Jazz” musician in the traditional sense, it is impossible to take note of rising Chicago artists without mentioning Sylvia Christine. The word jazz is amorphous enough, anyway. A Woodlawn-native and childhood musical prodigy, Christine’s music uses creative expression as a mode of communal love and healing. Spiritual at heart yet minimalist in nature, Christine experiments with stripped down ukulele, homemade indie production, and spoken word poetry in albums that feel simultaneously ethereal and raw. In that sense, she is a jazz musician.

Must-listen:

Christine’s debut full-length album, 2021’s Who?, is a perfect encapsulation of her stylistic fusion and potential. Opener “2.20.2020” is a soft spoken word piece put over minimalist synths and piano hits. It introduces the listener to Christine as a person. “STOP!” is slinky and layered like something from Solange. “B.Y.K” and “Sent” are both stripped down guitar-focused tracks, placing the focus on Christine’s intimate lyrical style. “Sent,” especially, has a sense of calming wanderlust to it, especially towards the end as she adds layers. The closer “Change” follows a similar path, but with a distinct, unshakable optimism.


edited by Nico Martin and Maria Kravtsova.

artwork by Wyatt Warren.

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