Classic Pac-Man arcade game screen with maze, dots, and four ghosts in the top left, and Pac-Man yellow character near the ghosts.
A man with curly hair and a beard, wearing a white shirt, against a bright yellow background.
A cartoon character with yellow skin and black hair lying on a blue couch, listening to music with headphones, looking relaxed.

 ALEX LESTER 

A stylized black Tyrannosaurus rex skull on a red background, enclosed in a yellow and white arched border.
A cartoon depiction of a meteorite with a gray, cratered surface, fiery orange and yellow trail, and white outline on a gray background.
Graphic of the Oregon state flag with the words 'Portland Oregon' written in yellow script.
Illustration of a classic handheld gaming device with a gray body, green screen, and red buttons
A clear glass of water on a yellow surface with a yellow background.

Chaotic Good Jazz

Chaotic Good Jazz brings together the things I care most about: listening deeply, sharing discoveries, and helping artists get their music heard. A weekly newsletter for music exploration, a radio show on Shady Pines Radio, and a bi-weekly program on Freeform Portland — all built around modern, cutting-edge, and experimental jazz. 

Fewer barriers, more connections. Recognized by the American Jazz Museum.

VISIT THE CGJ WEBSITE

Stats (August 2026):

Substack - 900+ subscribers / 1.25k followers / 4.5k 30d views

Instagram - 1k+ followers / 13k views 30d views

ARTISTS INTERVIEWED ON AIR:

BrandonLee Cierley

PoiKilo

Negative Concord

Bendrethegiant

Cochemea

Brandon Woody

Reed Wallsmith (Blue Cranes)

Jeremy Famà

Domo Branch

Lo Steele

BrandonLee Cierley PoiKilo Negative Concord Bendrethegiant Cochemea Brandon Woody Reed Wallsmith (Blue Cranes) Jeremy Famà Domo Branch Lo Steele

An abstract, digital illustration featuring a stylized, colorful representation of the number 16 on a vibrant, patterned background.
Pattern of overlapping, colorful numbers and shapes in blue, yellow, red, and white.
Bright yellow text with black outline spelling 'CHAOTIC GOOD JAZZ' over a blue patterned background with overlapping outlined words. Additional white and yellow text below indicates a radio show hosted by Alex Lester on Shady Pines Radio, airing Frid
A colorful poster promoting a radio show called 'Chotic Good' hosted by Alex Lester, featuring new music Mondays on Freeform Portland station 90.3/98.3 FM.
A MacBook Air laptop on a wooden desk displays a website called 'Chaotic Good Jazz' with various album reviews and listings. In the foreground, there is a smartphone face down on the desk.
Close-up of a woman holding a smartphone with a music playlist titled 'Chaotic Good Jazz' on the screen, while wearing earphones and a black wristwatch.
A smartphone displaying the Instagram profile of chaoticgoodjazz, with a vibrant background of blue and yellow graphics and social media content, set against a dark, red and blue illuminated environment.
A collage of four colorful music-themed posters and charts, featuring titles like "FACING THE SUN," "TRAPO CASUAL," "HEADWATERS OF THE SOUL," and a diagram titled "UNIT OF TIME" with various musical and rhythm notations.
A colorful, abstract background with a black scribbled pattern of text overlay titled "Nightmare". The text includes sections labeled "Intro" with "Frantic", "AHHHHH!!!!!", "Mwahahaha!!!", "Building Tension", "Driving & Panicky", and "Intense Outro".
A music waveform visualization over a background of tree branches with autumn leaves and sky. The overlay includes text with song and artist information, and annotations describing the musical elements such as 'mysterious & ethereal,' 'subtle saxopho
Poster promoting Jazz Appreciation Month with a lineup of jazz performers, event details, and graphics for a radio show called 'Chaotic Good Jazz with Alex Lester,' scheduled for Friday, April 17th from 10 AM to Noon Pacific.
A collage of posters and artwork related to jazz music, with prominent text overlay stating 'January 2026' multiple times in yellow and blue fonts.
Event poster titled 'Chaotic Good Jazz on Shady Pines Radio' scheduled for March 27, 2026, featuring a list of jazz performances and artists on a blue patterned background with yellow and orange text.
A colorful poster for the 'Chaotic Good Jazz with Alex Lester' radio show, listing performances scheduled for May 4th, 2026, including various jazz artists and song titles, with blue, yellow, orange, and black design elements.

RECOGNITION

“Curated playlists from the adventurous edges
of modern jazz.”

— American Jazz Museum

“Great weekly jazz recommendations.”

— Matt, Sonic Explorations

“Great weekly deep dive into an enormous amount of new music. Well designed graphics and thoughtful presentation.”

— Jonas Jacobs, Penguin Jazz A-Z

“Alex has really made this Substack and his radio show something special with his energy and enthusiasm and taste.”

— Adam Sieff, Jazz on the Beach

2026 Portland Jazz Festival

Original content for PDX Jazz spanning the full festival. It was a fantastic year of music and I’m already looking forward to next.

  • Newsletter preview of festival

  • On-air artist interviews hosted on Chaotic Good Jazz on Shady Pines Radio with:

    • Cochemea

    • Brandon Woody

    • Reed Wallsmith (Blue Cranes)

  • Live event social media coverage & recap reel

  • Graphic design (stop-motion + digital animation, giveaway graphics, social posts)

A man playing the trumpet on stage with drums behind him and music equipment around him.
Decorative signs with band names and a schedule, featuring large illuminated letters spelling 'JAZZ', neon signs saying 'JAZZ' and 'The Jack London Bar', and a letter board with the names 'CHARLIE HUNTER TRIO'.
Poster for the Portland Jazz Festival featuring Shady Pines Radio, a chance to win tickets, and performances by Cochemea and Dreckig at Holocene on March 10, 2026.
Man playing a saxophone on stage with colorful lighting and sound equipment.

WATCH THE FESTIVAL STORY RECAP! FOR SOUND, WATCH ON INSTAGRAM ↗

VARIOUS DESIGN, ANIMATION, AND CREATIVE PROJECTS…

Stop-motion and digital animation, graphic design across print and digital — spanning client work and personal projects.

Cartoon of a lava lamp with green liquid and bubbles inside on a light blue background.
Event poster for William Temple House Jam featuring musical acts and a raffle prize for tickets, scheduled for May 9th from 2 to 8 pm, with performers including Emma Sameth, Vibralocity, Aslin, Ned & Wendy, The Band, Jeremy Famà, and Frecks, promotin
A promotional retractable banner displaying a superhero character wearing a blue costume with a red cape and a golden emblem on the chest, standing next to a colorful comic book style design. The banner promotes NOLASTRAY SUPPORT, encouraging honesty
A tabletop with a box of Powells Books, a bowl of popcorn, a bowl of colorful candies, a bag of Smart Sweets, a bowl of purple and blue candies, and four cans of soda.
A plain, light beige or cream-colored background with no distinct objects or details.
White T-shirt with a colorful design featuring a yellow trumpet and the word "JAZZ" in red capital letters.
A classic Pac-Man arcade game screen with the maze, four Pac-Man ghosts, and a yellow dot.
Halloween-themed illustration with a haunted house, a bat, a tombstone marked 'R.I.P.', a zombie boy and a ghost, autumn-colored trees, and the word 'October' in colorful letters.
Comic-style illustration of a superhero with a yellow and red mask, blue costume with a fleur-de-lis emblem, cape, and gold arm wraps, standing above a support sign with an explosion graphic.
A group of white and pink plush stuffed animals with a humanoid appearance, sitting on a wooden surface in front of a pale green wall.
A person in a suit with a superhero mask and cape, holding open their shirt to reveal a symbol of a fleur-de-lis on their chest.
A breakfast table with a bowl of oranges, multiple bowls of chickpeas, glasses of coffee, a glass of orange juice, and a package of Panda Puffs cereal.
A circular graphic with the phrase 'TEMPLATE' in large, bold letters at the top, and intricate, detailed patterns and illustrations, including buildings, a bicycle, and various decorative elements, filling the interior of the letter shapes.
A close-up of a transparent plastic spray bottle with a white pump, placed on a light blue surface.
The word 'ZIGZAG' with silhouettes of people performing various outdoor activities like skiing, rock climbing, mountain biking, and hiking around and on the letters.
Logo with the words "Jazz Strology" in black and white, featuring a treble clef integrated into the letter "O" in "Strology".
A computer game screen featuring a bouncing ball and a black paddle at the bottom against a turquoise background.
A clear glass bowl filled with water against a yellow background.
Colorful cartoon logo with a mouth open wide and rainbow, featuring the text 'Camp Bites'.
A graphic with a brown splash background, featuring a white bubble tea cup with tapioca pearls, and the text 'BURST BO BA' with a smiley face inside the letter 'O' in 'BO'.
A can of SunSip cherry cola flavored soda with benefits, placed against a pink background.
REI Co-op logo with mountain and pine tree graphic
Kitchen shelf with bottles of olive oil, a jar of pasta, three boxes of Banza pasta, a basket of red onions, and cans of chickpeas.
Black and white sesame seeds arranged in a spiral on a light blue background.
A jar of Chia Smash raspberry superfood jam with raspberries scattered around it on a blue background.

ALEX

LESTER

2026 ALEX LESTER | PRIVACY POLICY