Comedian and actor Hannibal Buress, the Emcee of the inaugural Bitter Jester Music Festival, July 4, 2006. Hannibal was the winner of our Comedy Competition that ran in 2006/2007.

bitter jester music festival previous winners and participants

A list of all winners going all the way back to the summer of 2006!

This page is under construction. Bear with us as we continue digging through our archives…

Comedian and actor Hannibal Buress performs his winning standup set on June 4, 2006 (upper left) and Emcees the 1st Annual Bitter Jester Music Fest on July 4, 2006.


17th Annual Bitter Jester Music Festival, 2023

Grand Champions: Scorched Waves
Runners-Up: Ur Mom
Honorable Mention: Heat Above

Preliminary Concert Winners: David’s House • Heat Above • Beekman • Free Joel

Wild Card Picks: Fightin’ Bob • Misplaced Religion • Scorched Waves • Ur Mom

Showcase Bands: Exit 122 • Livingroom


16th Annual Bitter Jester Music Festival, 2022

Grand Champions: Summer Drive
Runners-Up: Summer League
Honorable Mention: Scorched Waves

Preliminary Concert Winners: Keep The Eleven • Scorched Waves • Fightin’ Bob • Summer Drive

Wild Card Picks: New Age Americans • Summer League • Fluctuation* • Venganza

(Listen to the Wild Card Bands announced by Dash, live on 101.9 The Mix New Music Club!)

Showcase Bands: Exit 122 • Opening Day

*Chainsaw Boyz had to withdraw; Fluctuation swooped in to the rescue!


15th Annual Bitter Jester Music Festival, 2021

Grand Champions: Summer Drive
Runners-Up: Pretoria
Honorable Mention: The Adem Dalipi Band

Preliminary Concert Winners: Venganza • Summer Drive • Quick and Painless • Pretoria

Wild Card Picks: Fluctuation • The Adem Dalipi Band • Quite Frankly the Band • Scorched Waves

(Listen to the Wild Card Bands announced by Dash, live on 101.9 The Mix New Music Club!)

Showcase Bands: Feed the Monkeys • Opening Day

2021 Grand Champions: Summer Drive (photo: Elliot Mandel)


First Ever Virtual Original Song Competition - “14.5th” Annual Bitter Jester Music Festival, 2020

Winner: “Keep Two Stepping” by Pretoria
2nd Place: “Shell City” by Feed the Monkeys
3rd Place: “Your Anything” by Double Identity
Honorable Mention: “Sleigh” by Tess Clare & Maddie Renner
Fan Favorite: “Collapse” by F.L.A.M.E.

Weekly Finalists: “The Beautiful Things You Do” (Ian Jake Robleza) • “Seven Stars” (Fluctuation) • “Shell City” (Feed the Monkeys) • “Keep Two Stepping” (Pretoria)

Weekly Fan Favorites: “Where My Life Remains” (Watchtower) • “Collapse” (F.L.A.M.E.) • “Peach Trees” (Ax and the Hatchetmen) • “Gentleman” (Quick & Painless)

Producer’s Picks: “Sleigh” (Tess Clare & Maddie Renner) • “Your Love for the End of the World (The Cuz) • “Your Anything” (Double Identity) • “Slouched” (Shipwreck Kelly)


14th Annual Bitter Jester Music Festival, 2019

Grand Champions: Cooper Run
Runners-Up: Ax and the Hatchetmen
Honorable Mention: Out of Pocket

Preliminary Concert Winners: Distant Cuzins (now “The Cuz”) • Quick and Painless • Cooper Run • Ax and the Hatchetmen

Wild Card Bands: Joyce Ln • Out of Pocket • Quick and Painless • The Recall • Through the Kitchen Hole

(Listen to the Wild Card Bands announced live on WBEZ by clicking here!)

Showcase Band: Augmented Seventh

2019 Grand Champions: Cooper Run (photo: Elliot Mandel)

2019 Grand Champions: Cooper Run (photo: Elliot Mandel)


2018 Grand Champions: The Isabel O. Trio (photo: Elliot Mandel)

13th Annual Bitter Jester Music Festival, 2018

Grand Champions: Isabel O. Trio
Runners-Up: Cooper Run
Honorable Mention: Out of Pocket

Friday Night Winners: Bad Idea • The Browns • Cooper Run • Out of Pocket

Wild Card Picks: 80HD • Ax and the Hatchetmen • Isabel O. Trio • Ghostbusterz (dropped out) • The Recall

Showcase Band: Fun Monkey (dropped out) • The Rand Band


12th Annual Bitter Jester Music Festival, 2017

Grand Champions: Audiophilia
Runners-Up: Livewire
Honorable Mention: Elise and the Police

Preliminary Concert Winners: Livewire • Audiophilia • Child of Eve • Surround Sound

Wild Card Picks: Eminence • Elise and the Police • The Magnifiers • Stellar West

Showcase Bands: Skydeck • The Browns

2017 Grand Champions: Audiophilia (photo: Elliot Mandel)


2016 Grand Champions: Caroline & The Priority (photo: Daniel Kullman)

11th Annual Bitter Jester Music Festival, 2016

Grand Champions: Caroline & The Priority

More info coming soon...


10th Annual Bitter Jester Music Festival, 2015

Grand Champions: PROFUSION

More info coming soon...

2015 Grand Champions: PROFUSION (photo: Daniel Kullman)


2014 Grand Champions: Xazz (photo: Daniel Kullman)

9th Annual Bitter Jester Music Festival, 2014

Grand Champions: Xazz

More info coming soon...


8th Annual Bitter Jester Music Festival, 2013

Grand Champions: Van Buren & Wells

More info coming soon...

2013 Grand Champions: Van Buren & Wells (photo: Daniel Kullman)


2012 Grand Champions: Midnight in Montana (photo: Daniel Kullman)

7th Annual Bitter Jester Music Festival, 2012

Grand Champions: Midnight in Montana

More info coming soon...


6th Annual Bitter Jester Music Festival, 2011

Grand Champions: JKZ

More info coming soon...

2011 Grand Champions: JKZ (photo: Daniel Kullman)


2010 Grand Champions: The Burrows Four (photo: Daniel Kullman)

5th Annual Bitter Jester Music Festival, 2010

Grand Champions: The Burrows 4

More info coming soon...


4th Annual Bitter Jester Music Festival, 2009

Tied Grand Champions: The Burrows 4 • Maq

More info coming soon...

2009 Grand Champions (tied): The Burrows 4 and Maq (photo: Ken Thompson)


2008 Grand Champions: The Railjacks (formerly "Drive") (photo: Terri Olian)

3rd Annual Bitter Jester Music Festival, 2008

Grand Champions: The Railjacks (formerly “Drive”)

More info coming soon...


2nd Annual Bitter Jester Music Festival, 2007

Grand Champions: Fat Lisa

More info coming soon...

2007 Grand Champions: Fat Lisa (photo: Terri Olian)


2006 Grand Champions: Drive (photo: Bev Beck)

2006 Grand Champions: Drive (photo: Terri Olian)

1st Annual Bitter Jester Music Festival, 2006

Grand Champions: Drive

More info coming soon...