Digging for Something with Alex Lester of Chaotic Good Jazz
Overlooked, underrated, over-hated or regionally specific gems.
I’m reaching out and asking writers, band members and music curators to tip us all off to their favourite underrated albums, overlooked or unfairly obscure gems… even the downright over-hated. Hopefully it’s another fun way for you to find some new-to-you music to love.
Joining me today is Alex Lester, the creator of Chaotic Good Jazz, a modern jazz newsletter and radio show exploring the textured, genre-blurring edges of jazz.
Each week, he shares playlists, listening notes, and occasional waveform doodles. You can also catch him live on Chaotic Good Jazz Radio, Fridays from 10–12 PT on Shady Pines Radio. He lives and listens in Portland, OR.
And now, let’s get to their album recommendations:
The Magic Triangle - Trapo Casual (2025, Self-Released)
Genres: Avant-Garde Jazz, Psychedelic Jazz
Alex says:
Released on January 9th, 2025, Trapo Casual was the first album of the year that I really fell in love with. The Vancouver B.C.-based sax/drum/bass trio blends Latin rhythms and psychedelic jazz in a genre-blending and blurring improvisation that was recorded in a single take.
Dan says:
Jazz is a genre I love and appreciate, but am surely no expert in. This edition of my series will likely show this as I try to grasp at comparisons and milestones for these sounds. To me, this feels quite a bit like The Bad Plus, in the way they are experimental and avant-garde while remaining melodic and groove-based. This sits exactly in my jazz sweet-spot, and I look forward to listening to this more.
Emma Dayhuff (feat., Isaiah Collier, Kahil El'Zabar, and Dee Alexander) - Innovations & Lineage: The Chicago Project (2025, Division 81 Records)
Genres: Spiritual Jazz, Vocal Jazz
Alex says:
Dr. Emma Dayhuff, educator, bassist, and member of the Esthesis Quartet, makes her stellar debut as bandleader connecting four generations of Chicago's most creative musicians in what has quickly become one of my favorite albums of the year. The album features "The Chosen One" Isaiah Collier (on this list for the second time as collaborator), Kahil El'Zabar's energetic and utterly infectious beats, as well as Dee Alexander's emotional and chill-inducing vocals.
Dan says:
This is really making me remember how thrilling and vital live jazz is. This sits juuust outside of something I would listen to over and over (more on Vocal Jazz later,) but the performances captured here are pretty incredible.
David Mitchell - Turiyans (2025, Self-Released)
Genres: Free Jazz
Alex says:
Turiyans is an album that incorporates a cinematic use of synthesizers and Central Asian influences. Inspired by Alice Coltrane and electric-era Miles Davis, Mitchell makes a commitment to achieving altered states of consciousness through sound in this collaboration with saxophonists Finn Peters and Guiseppe Doranzo.
Dan says:
Another one that is pretty outside the realm of my jazz knowledge, but that I found very fascinating. In particular the droning synths on tracks like “Phase Space” really captured my interest. Also the rhythms on the title track were quite hypnotic.
Brittany Davis - Black Thunder (2025, Loosegrove Records)
Genres: Vocal Jazz, Spiritual Jazz, Contemporary R&B, Poetry, Neo-Soul
Alex says:
Brittany Davis, the multi-instrumentalist who has been blind since birth, released her sophomore album Black Thunder on June 13, 2025. The entire album is incredible, but "Amid the Blackout of the Night" is a profound and immersive track that has literally moved me to tears while listening.
Released on Loosegroove Records (a label founded by Pearl Jam's Stone Gossard), I cannot recommend it enough.
Dan says:
OK, sounding like a broken record, but Vocal Jazz is yet another corner of jazz that isn’t found in my listening rotation all that often. Hearing stuff like this makes me want to change that, though. Another album that I want to call hypnotic. “All You Get” is an incredible opening track and as Alex mentions, “Amid the Blackout of the Night” follows it and is a highlight as well.
Theon Cross - Affirmations (Live) (2025, Self-Released)
Genres: Jazz Fusion, Afro-Jazz
Alex says:
Jazz tuba innovator Theon Cross unleashed a live Afro-Carribean-influenced album to the world on July 11, 2025 that needs to be listened to, not just heard. The album features saxophonist Isaiah Collier, guitarist/bassist Nikos Ziarkas, and dummer James Russell Sims and was recorded at the legendary Blue Note NYC. I played tuba in my middle school through university bands, so I really appreciate Cross' work highlighting an often under-utilized instrument in jazz.
Dan says:
Really wasn’t sure what to expect from this after the opening “Greetings”, but damn they dive straight into some intense tuba-led funky jazz and it got my toes tapping for sure. The drumming on this live performance alongside some of the atmospheric guitar work (the piercing, delayed notes on “We Go Again”) really seals the deal in support of the phenomenal tuba work. I think you can actually hear the tuba rattling glasses in the room on “Leap of Faith”?!
That’s it, that’s all. Be excellent to one other.
I knew you'd dig The Magic Triangle! I really enjoyed putting this list together and sharing it with you and your readers.
Thanks again!