Seattle has a habit of producing musical anomalies. It is the hometown of Jimi Hendrix, Quincy Jones, and now, drummer and composer Kassa Overall. Like those iconic trailblazers, Overall refuses to fit neatly into any predefined genre.
His latest album, Cream, is the ultimate proof.
Hanging out at the Montreal Jazz Festival, the 43-year-old musician broke down the paradox of his new project to me.
“It’s funny, the most acoustic record I’ve made is a hip-hop record. The whole album is covers of rap songs from the 90s that inspired me. I purposely chose songs that, growing up, expanded me musically. We took the harmony or the rhythm or the arrangement and tried to recreate those songs as if we were reimagining making a jazz record in the 60s. We even recorded it in one room.”
Imagine classic hip-hop joints by the Wu-Tang Clan, The Notorious B.I.G., and Digable Planets sounding as if they were being played by the Jazz Messengers, Antonio Carlos Jobim, or Joe Henderson. Cream is 99 percent acoustic, utilizing the aesthetic of 1960s jazz to mash up the heavy-hitting hip-hop records of the 1990s.
The self-described avant-gardist is a walking dichotomy. He proudly shouts out his time walking the creative high wires with boundary-pushers like pianist Vijay Iyer and saxophonist Steve Coleman (a musician so “out” he created his own sub-genre, M-Base).
“Hey man, I’m from Seattle, we’re known for being a bit out there,” Overall laughed. “That’s me, way more than inside.”
Yet, his influences range from arty free jazz to the most commercial hip-hop imaginable. Overall sees a distinct through-line between the two:
“The interesting similarity with hip-hop producers and composers is that when they’re dealing with sound, like an avant-garde musician, they’re not necessarily interested in chord progressions as mathematics. If you listen to a Public Enemy beat or certain underground West Coast productions, sometimes a chord produces a weird dissonance, and that dissonance inspires a story...”
This is exactly what the Art Ensemble of Chicago and the World Saxophone Quartet do. It is no wonder this Grammy-nominated musician won the prestigious Doris Duke Artist Award last year and the Arts Innovator Award two years prior.
For many listeners, Cream will act as a massive Gateway Album. Just as hearing Al Jarreau sing “Take Five” forced me to go back and discover Carmen McRae’s version, younger jazz fans might find themselves seeking out Biggie Smalls after hearing Overall’s acoustic “standards.”
Take his reimagining of Biggie’s “Big Poppa.” Overall recognized a hidden nuance in the legendary Brooklyn rapper’s delivery:
“Biggie’s tone... his restraint reminded me of a Brazilian singer. The Brazilian singers in that bossa-nova space are always light with that restraint. When you listen to Biggie rap, most of the time he’s cool; he uses that same kind of restraint like he’s in the club rapping in your ear.”
The genius of the track lies in its multiple entry points. The original Biggie version famously sampled the Isley Brothers’ 70s R&B classic, “Between The Sheets.” Overall cleverly embedded that intoxicating riff into his acoustic pastiche, layering bossa nova, jazz, and hip-hop into one cohesive statement.
“We’re creating a cultural time machine,” Overall concluded. “The song that we’re making sounds older than the original we’re covering. Biggie came out in the 90s, the Isleys’ in the 70s, and here we are in 2026 taking it back to bossa nova.”
(Also receiving the jazzed-up hip-hop treatment on Cream: Outkast, A Tribe Called Quest, and Juvenile).
Live from FIJM 2026: Montreal is Still the Undisputed King of Jazz Fests
When Montreal Jazz Festival founders Andre Menard and Alain Simard handed over the reins three years ago, they likely knew it was time for a younger perspective. Jazz is growing younger, and festivals across the globe are reflecting that shift.
The 2026 Festival International de Jazz de Montreal (FIJM) marked the 46th annual iteration of the event, but just the third under Director of Programming Maurin Auxemery. As a veteran well into my third decade of trekking to Quebec every July, I still insist that the Montreal Jazz Festival is the best in the world.
Under Auxemery and his chief assistant programmer, Modibo Kieta, it has somehow gotten even better!
Because the free stages were so compelling, I didn’t hit too many paid shows, but the ones I did see were spectacular. Standouts included Joshua Redman, a masterful duet between Christian McBride & Julian Lage, and Melody Gardot performing with the incredible Thanda Choir from South Africa.
As my love affair with this event deepens, I’ve tried to bring more friends and family into the fold. Normally, I stay just long enough to cover the five days needed for my SiriusXM broadcasts. But with my all-time favorite band, Earth, Wind & Fire, closing out the festival, I extended my stay to nine days.
That gave my wife and me enough time to host three different groups of visiting friends, including my friend Judy Matthews (returning from last year) and my brother Clifford with his wife Cyndi. (I’m fairly certain Clifford is already booking his flights for next year).
The City of Saints had one more surprise for us before we left, as we’d get to join the parade festivities of Carifête - The annual Carimas Festival. The vibrant multicultural celebration showcased Caribbean culture with colorful floats, elaborate masquerade costumes, steelpan bands with soca and calypso music. Valerie and I absolutely adored the entire experience. There’s a reason this event is in the Guinness Book of World Records as the largest jazz festival on the planet.
I will absolutely be back. Come join me in 2027!
The most glaring evidence of FIJM’s growth is the explosion of high-quality, free programming. A massive percentage of this festival has always been free, but the sheer caliber of artists accessible to the public is staggering.
Broadcasting daily on SiriusXM Real Jazz, I can request access to virtually any paid show. This year, I was amazed at how rarely I had to bother the press office. Without spending a dime, I was able to catch:
Kamasi Washington
Brandee Younger
Nicholas Payton with Butcher Brown
Domi & JD Beck
Willow
Elena Pinderhughes
Kassa Overall
This programming is a powerful statement. The adventurous, edgy jazz of right now needs to be heard by the young (who may not have the money) and by the old (who may not have the ears). Montreal is the ultimate landscape for discovery.
I’ve always told friends that aside from travel and lodging, spending a lot of money on music isn’t mandatory here. FIJM prides itself on the quality control of its free acts. A decade ago, I had a paid festival admission to see the then-unknown Catherine Russell. I got stopped in my tracks on my way to the mainstage by a captivating set featuring The Psychedelic Soul Orchestra playing the music of Minnie Riperton. Then, just as I was beginning to peel myself away from that stage, Steely Dan and his African Band held me captive there with their dynamic sound. By the time I finally made it to the main stage, I had missed Catherine’s set completely, but fortune was still smiling in my favor from the amazing musicians I took in.
That is the magic of a festival boasting twenty performance spaces (ten of them outdoors)! So if you’re still not convinced, you can check out their Instagram for more of their coverage.
As always, I want to share some of my latest favorites in my ongoing collection of Gateway Jazz before I sign off. What are you listening to in your jazz life? Join the community and drop some tunes in our chat:
“Coherence” - Cindy Blackman Santana
Mack Avenue
“A Supreme Blue” - Nicholas Payton & Butcher Brown
Concord
“Last Train to Sanity “ - Stanley Clarke
Roxboro Entertainment
“Slight Accent” - Ray Obiedo
Rhythmus
“No Wind, No Rain” - Chicago Soul Jazz Collective
Calligram
Thanks for checking out this issue of My Jazz Life! I’ll see you later this month for another issue. Until then, thanks for reading and listening. Swing safely out there folks.
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