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Alex Lester

@_alexlester_

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followers

636

following

I'm a jazz listening, sports watching, plant-eating, doodling dude
Follow @chaoticgoodjazz for jazz recs
📍 Portland, OR • ⛷️🧗🏃🍄🥦⚾

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2026 @montavillajazzfest headliner @losteele and I had a chance to chat on @shadypinesradio on Friday, which was the first day of the Montavilla Jazz Festival.

Hear our conversation about this year's festival, collaboration with the legend @charliehunterguitar , and a little bit about musical theater in the MixCloud archive (link in bio).

Don't miss Lo performing with @greaterkind Sunday September 6th at the Mt. Tabor Caldera Amphitheatre. Weekend passes available at montavillajazz.org

#jazz
#jazzradio
#shadypinesradio
#chaoticgoodjazz
#montavillajazzfestival taken in Portland, Oregon by @_alexlester_

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a month ago

@montavillajazzfest 2026 performer @domobranch joined me last week on @shadypinesradio to talk about his upcoming performance at @showbar.pdx , his 2025 album 'Hand of Gifts', and more!

Listen to the full episode archived on @mixcloud featuring more Montavilla Jazz Fest performers: @losteele @greaterkind @marquezmusic @alea_loren @and.or_you @abandcalledonion @outerorbitband @brandonleecierley @warptrio

Domo selected some songs for this episode and I'm also highlighting some special guests to this year's festival @alden.hellmuth and @braxton_cook

And closing things out is some disco-era Dolly, a soulful cover of "Jolene" and a funky rendition of "9 to 5".
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The Montavilla Jazz Festival takes place September 4-6th, tune in next Friday 10-Noon Pacific for my conversation with festival headliner Lo Steele.

#jazz #chaoticgoodjazz #montavillajazzfestival #shadypinesradio #jazzradio taken in Portland, Oregon by @_alexlester_

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2 months ago

During my formative teenage years, few artists had a bigger influence on my listening habits than A Tribe Called Quest.

So after falling down a 'who sampled' rabbit hole, this week's Chaotic Good Jazz @shadypinesradio show features 2 full hours of 70's era jazz-funk that has been sampled on some of the Tribe's most iconic tracks.

Here's the breakdown of the show:

"Jazz (We've Got) shares some musical DNA with Jimmy McGriff's "Green Dolphin Street" and The Five Stairsteps "Don't Change Your Love."

"Bonita Applebum" samples "Daylight" by Ramp, Rotary Connection's "Memory Band" and "Jagger the Dagger" from Eugene McDaniels.

"Electric Relaxation" features samples from "Mystic Brew" - Ronnie Foster, Ramsey Lewis' "Dreams" from the album 'Funky Serenity', and the drums from the Brethren's "Outside Love."

"Can I Kick It?" consists of samples from "Spinning Wheel" by Dr. Lonnie Smith, as well as Dr. Buzzards Original Savannah Band with "Sunshower" and "Fun" from Sly & The Family Stone and more!

In the second hour you'll hear the source material behind:

Award Tour"
- "Olinga" - Milt Jackson
- "We Gettin' Down" - Weldon Irvine
- "Lowdown" - Charles Earland

"Scenario"
- "Oblighetto" - Brother Jack McDuff

"Butter"
- "Gentle Smiles (Saxy)" - Gary Bartz
- "Young and Fine" - Weather Report

"Description of a Fool"
- "Running Away" - Roy Ayers Ubiquity

"Vibes and Stuff"
- "Down Here on the Ground" - Grant Green

"I Left My Wallet in El Segundo"
- "Funky" - The Chambers Brothers
- "Seuno" - The Young Rascals

Listen live on Shady Pines Radio or on demand via MixCloud (link in bio) and come hang out this Sunday (8/23) @vebrewing (825 N Cook St) for pizza, pints and plenty of funky jazz (2-5pm)

#jazz
#jazzradio
#shadypinesradio
#communityradio
#atribecalledquest taken in Portland, Oregon by @_alexlester_

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2 months ago

FREE PIZZA & FUNKY JAZZ

🗓️ Sunday, August 23rd
📍825 N. Cook St. | @vebrewing Mississippi Taproom
🎵Funky tunes by @chaoticgoodjazz from 2-5pm
🎈Balloon Animals by Connor

Get a FREE Detroit-style slice at the Von Ebert Brewing Pizza Pop-Up on August 23rd by donating to the @oregonfoodbank anytime during the month. Bring your donation receipt on Sunday to claim your slice.

Come hang out, support your local community, grab a pie and pint, and enjoy the jazz!

#chaoticgoodjazz #vonebertbrewing #oregonfoodbank #portlandoregon #portland taken in Portland, Oregon by @_alexlester_

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2 months ago

Tune in every Friday 10am-Noon Pacific on @shadypinesradio for the wild, the weird, and the deeply groovy corners of modern jazz.

Hosted by @_alexlester_ , each episode is a curated journey through experimental cuts, spiritual grooves, acid jazz bangers, and off-the-rails saxophone solos.
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& come hang out and enjoy a pizza pie at @vebrewing (825 N Cook St) on Sunday, August 23rd. I'll be spinning some tunes while you enjoy your brews from 2-5pm.

#jazz
#musicdiscovery
#chaoticgoodjazz
#shadypinesradio
#vonebertbrewing taken in Portland, Oregon by @_alexlester_

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2 months ago

My Favorite 8 Modern Jazz Albums 🎷

These are my desert island albums, the ones I never get tired of, the ones that hit just right all the way through... every.single.time.

Some of these will undoubtedly be familiar, but I hope some of these are still under-the-radar enough to be “new-to you”.

If you've been following along for a while, you know I love to cover the best new releases out each week, but last week I shared my all-time favorite 8 modern jazz records on Substack.

If you're not already subscribed, I really hope you'll check it out (link in bio) and Discover Something Different 🛸

Polar Bear - Same as You

Infectiously groovy spiritual jazz from Sebastian Rochford, Tom Herbert, Leafcutter John, Pete Wareham, Mark Lockheart and Hannah Darling, with guest saxophonist Shabaka Hutchings.

“Don’t Let The Feeling Go” is a serious earworm and your brain won’t be able to let the melody go.

@sebrochford
@electrobeard
@leafcutterjohn
@warehampete
@marklockheart
@shabakahutchings
@editionrecords

Tom Skinner, Tom Herbert, Dave Okumu - Undone: Live at the Crypt

The first of four live albums on this list. Bassist Tom Herbert (also a member of Polar Bear), drummer Tom Skinner, and guitarist Dave Okumu collaborate on an energetic and groove-filled jam session.

@tomskinnermusic
@electrobeard
@dave_okumu_
@thevinylfactory

Sarathy Korwar - My East Is Your West

Live Indo-inspired spiritual jazz from percussionist Sarathy Korwar, featuring Tamar Osborn on bari sax and flute throughout the album, as they cover Don Cherry, Pharaoh Sanders, Joe Henderson, Alice Coltrane and more.

@sarathykorwar
@tamarosborn
@gearboxrecords

Timo Lassy and Teppo Mäkynen - Live Recordings 2019-2020

This We Jazz release has been one of my favorites to share on my radio show and in my newsletter. “Zomp”, “Kobi”, and “Solution Black” are some of my personal favorite tracks, but there's really no going wrong once this sax and drum duo of Lassy and Mäkynen gets going.

@timolassy
@teppomakynen
@wejazzhelsinki

Work Money Death - Thought, Action, Reaction, Interaction

This is the pinnacle of modern spiritual jazz. ATA Records broke the scale against which I compare all oth by @_alexlester_

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2 months ago

This week's @shadypinesradio show features a few of the artists performing at @pickathon including the soulful sounds of @thealtons @thewomacksisters @familycompanymusic and the perpetually groovy Okzat-Ozkat ( @or.similar.records )

Tune in to Chaotic Good Jazz this Friday, July 31 from 10am-Noon Pacific for 2 hours of modern jazz and more!

And don't miss Okzat-Ozkat at Pickathon on Saturday (8/1) 2pm | Farmhouse.

#shadypinesradio
#communityradio
#jazzmusic
#musicdiscovery
#chaoticgoodjazz

Visual created using projectM taken in Portland, Oregon by @_alexlester_

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3 months ago

Discover Something Different 🛸

This week's newsletter and @shadypinesradio show will focus on some of my absolute favorite modern jazz albums, including this @wejazzhelsinki release from @timolassy & @teppomakynen

Tune in Friday, July 31, 10am-Noon Pacific on shadypinesradio.com or the amazing Shady Pines app and follow along with the Chaotic Good Jazz Substack so you never miss a playlist or a post 🎷

#shadypinesradio #chaoticgoodjazz #jazz #jazzmusic #musicdiscovery

Visual created using projectM taken in Portland, Oregon by @_alexlester_

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3 months ago

@shadypinesfestival 2026 was outta this world 🛸

Chaotic Good Jazz has been on @shadypinesradio for a little over a year, but this was my first time out at Camp Tasty's | @try.tastys for the festivities and I'm already excited for 2027!

The weather was perfect, @johnnythefranco and @realbrotherdom , @rebandthegoodnews , @sweetnjuicymusic & @bendrethegiant put on some incredible performances Sunday afternoon on the rainbow stage...and I had the honor of spinning a couple sets from the UFO themed DJ stage in between performances.

Tune in on Friday (7/24) for a replay of my set from 10am-Noon Pacific on the pinewaves or check out the full uninterrupted 90 min mix on Mixcloud (link in bio.)

#chaoticgoodjazz
#shadypinesradio
#shadypinesfestival2026
#jazz
#communityradio taken in Portland, Oregon by @_alexlester_

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@_alexlester_ is the creator of @chaoticgoodjazz, a modern jazz newsletter and radio show that explores the textured, genre-blurring edges of the jazz landscape. Each week, he curates playlists and commentary that push the boundaries of contemporary jazz. Catch him live on Chaotic Good Jazz Radio, Fridays from 10–12 PM PT on Shady Pines Radio. Catch them at @shadypinesfestival!

Grab tickets now at ShadyPinesFestival.com — link in bio! taken in Camp Tasty’s by @_alexlester_

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4 months ago

𝗖𝗵𝗮𝗼𝘁𝗶𝗰 𝗚𝗼𝗼𝗱 𝗝𝗮𝘇𝘇
𝗔𝗹𝗯𝘂𝗺𝘀 𝗼𝗳 𝘁𝗵𝗲 𝗠𝗼𝗻𝘁𝗵
𝗠𝗮𝘆 𝟮𝟬𝟮𝟲

May was my 1-year broadcast anniversary on @shadypinesradio and it's been one of the strongest months of new releases since I started sharing music with you all.

May's full monthly roundup is live on the Chaotic Good Jazz Substack (link in bio.)

My last 30 days of listening distilled into the (chaotic) good stuff, including some under-the-radar finds and a few favorites that dropped this month.

New-to-me this month: @youmethewhales @strachantrumpet @plasticwasteband

CGJ favorites with new releases: @hatehyphendash @sneakyjesusband @laurenzpike

Plus two Portland duos you need to hear: @themerkababrotherhood ( @romannorfleet & @brown_calvin ) and GAMSIM ( @instagambz & @simpsonaire )

This month's categories:
🪐 Cosmic & Spiritual Jazz
🌍 Global Jazz Fusion
🔥 Avant-garde & Free Jazz
🎶 Modal Jams & Improvisational Grooves
🎺 Post-Bop & Contemporary Hard Bop
🌊 Ambient & Electronic taken in Portland, Oregon by @_alexlester_

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4 months ago

This Friday (5/22) is my 52nd episode of Chaotic Good Jazz on @shadypinesradio

I've played over 1000 songs in my first year of broadcasting on the pinewaves and this week I'm replaying a few of my favorite tracks and a couple new-to-me jams that I can't get out of my head.

Download the app and come say hey in the chat!

Tune in this week, 10am-Noon Pacific to hear music from:
@timolassy
@theon_cross
@captainbessiesuave
@bendrethegiant
@brandonleecierley
@outerorbitband
@officialsoulive
@uffesteenofficial & @vestbotrio
@sheets0fsound
@rosabrunello
@kahilelzabar
@colliersworld

#shadypinesradio #musicdiscovery #chaoticgoodjazz taken in Portland, Oregon by @_alexlester_

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5 months ago