Comedian and actor Hannibal Buress, Emcee of the inaugural Bitter Jester Music Festival, July 4, 2006, holds his prize check. Hannibal was the winner of our 2006 Comedy Competition that ran from 2006-2009. Subsequent winners include Scott Derenger (2007), Jim Zekis (2008), and Drew Michael (2009).
Previous Bitter Jester Music Festival Winners and Emcees
A list of all Winners, Medalists, and Grand Finale Emcees going all the way back to the summer of 2006!
We are digging through our archives to continually update this page. More info is added periodically!
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.
20th Annual Bitter Jester Music Festival, 2026
Grand Champions: Exit 122
Runners-Up: Belle Vista
Honorable Mention: Cabin Fever
Preliminary Concert Winners: Exit 122 • Taranis • THREEGON • Tripsitter
Wild Card Picks: Mistrophia • Cabin Fever • Hammerhedd • Belle Vista
Showcase Bands: Billy Schaumann • Izzy Savides • Mystik • The Strolls
Featured Guest Artist Claire-Mckenna
Grand Finale Emcees: Nicolas DeGrazia & Peter Sagal
19th Annual Bitter Jester Music Festival, 2025
Grand Champions: Platinum Moon
Runners-Up: Charlieboy
Honorable Mention: Exit 122
Preliminary Concert Winners: Meera Raphael • Patches & Albo • Platinum Moon • Exit 122
Wild Card Picks: TIKIMEN OF BERLIN • Charlieboy • ZEKE ROWAN • Cabin Fever
Showcase Bands: rae • Crowd Vulture • The Orchids • North Grove
Grand Finale Emcees: Nicolas DeGrazia & Peter Sagal
18th Annual Bitter Jester Music Festival, 2024
Grand Champions: Ur Mom
Runners-Up: Scorched Waves
Honorable Mention: Lauren Blackford
Preliminary Concert Winners: Scorched Waves • Ur Mom • Heat Above • VenganzA
Wild Card Picks: VICK LUNA • Lauren Blackford • Sunset Drip • Exit 122
Showcase Bands: North Grove • Anna Louise Bramlett
Featured Guest Artist: rae
Special Mention: Charlieboy
Grand Finale Emcees: Nicolas DeGrazia & Peter Sagal
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: Livingroom • Exit 122
Featured Guest Artist: East of Vilas (withdrew) • Polly on the Wall
Grand Finale Emcees: Nicolas DeGrazia & Meg Grunewald
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 • Chainsaw Boyz* • Fluctuation* • Summer League • VenganzA
(Listen to the Wild Card Bands announced by Dash, live on 101.9 The Mix New Music Club!)
Showcase Bands: Opening Day • Exit 122 (formerly “F!reworks”)
Featured Guest Artist: Linda Therese
Grand Finale Emcee: Nicolas DeGrazia**
*Chainsaw Boyz had to withdraw; Fluctuation swooped in to the rescue!
**Ryan Badger was scheduled to Co-Emcee on July 4, 2022 and was unable to attend the reboot concert in September. He sent a heartfelt message which Nic read to the crowd (and which appears as a special track on “Live at Bitter Jester Music Festival, vol. 01”)
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
Featured Guest Artist: Info Coming Soon…
Grand Finale Emcees: Nicolas DeGrazia & Meg Grunewald
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: The Recall • Through the Kitchen Hole • Out of Pocket • Joyce Ln
(Listen to the Wild Card Bands announced live on WBEZ by clicking here!)
Showcase Band: Augmented Seventh
Featured Guest Artist: Hutch Hoepner
Grand Finale Emcees: Nicolas DeGrazia & Elizabeth Krahulec
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: The Browns • Bad Idea • Cooper Run • Out of Pocket
Wild Card Picks: 80HD • Isabel O. Trio • Ghostbusterz (dropped out) • The Recall • Ax and the Hatchetmen
Showcase Band: Fun Monkey (dropped out) • The Rand Band
Featured Guest Artist: The Child of Eve
Selected to Perform at Navy Pier (7/13/18): Monarchy Over Monday
Selected to Perform at the Taste of Highland Park (8/24/18): The Rand Band • Double Identity
Grand Finale Emcees: Nicolas DeGrazia & Elizabeth Krahulec, with Aiden Kinsella as Assistant Emcee and Co-Host
12th Annual Bitter Jester Music Festival, 2017
Grand Champions: Audiophilia
Runners-Up: LiveWire
Honorable Mention: Elise and the Police
Preliminary Concert Winners: LiveWire • Audiophilia • The Child of Eve • Surround Sound
Wild Card Picks: Eminence • Stellar West • Elise and the Police • The Magnifiers
Showcase Bands: The Browns • Skydeck
Featured Guest Artist: No Results
Fourth Fest (Morning) Band: Double Identity
Grand Finale Emcees: Nicolas DeGrazia & David Vox Mullen
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
Runners-Up: Audiophilia
Honorable Mention: FUTURE STUFF
Preliminary Concert Winners: FUTURE STUFF • Not Now, Son • Audiophilia • Elise and the Police •
Wild Card Picks: Alabaster • Say I'm Pull • Caroline & The Priority • Clear Confusion
Showcase Bands: Double Identity • Graphic
Featured Guest Artist: Claud Mintz
Fourth Fest (Morning) Band: Stellar
Grand Finale Emcees: Nicolas DeGrazia & Meg Grunewald
More info coming soon...
10th Annual Bitter Jester Music Festival, 2015
Grand Champions: PROFUSION
Runners-Up: Xazz
Honorable Mention: The Ska-lers
Preliminary Concert Winners: The Ska-lers • North Korean Beach Party • Xazz • Van Buren & Wells
Wild Card Picks: PROFUSION • Senna • Saint Nicholas Cage
Showcase Bands: Via Clara • Elise and the Police
Featured Guest Artist: Meryl Rudy
Grand Finale Emcees: Nicolas DeGrazia & Meg Grunewald
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
Runners-Up: Trending Rex
Preliminary Concert Winners: Dead Yet Alive • Saint Nicholas Cage • Trending Rex • Xazz
Wild Card Picks: Van Buren & Wells • The Ska-lers
Showcase Bands: Havenway • Bloody Mary
Featured Guest Artists: Ava Suppelsa • Tess Considine • Sam Poll
Grand Finale Emcees: Nicolas DeGrazia & Daphne Scott
More info coming soon...
8th Annual Bitter Jester Music Festival, 2013
Grand Champions: Van Buren & Wells
Runners-Up: Avocado Baptism (formerly Midnight in Montana)
Preliminary Concert Winners: JKZ • Sam Poll • The Ska-lers • Avocado Baptism (formerly Midnight in Montana)
Wild Card Pick: Van Buren & Wells
Standby Band: Fruitful Dave
Special Mention: Circus Freaks (formerly Footsie with Suzie (formerly Gazebo))
Grand Finale Emcees: Nicolas DeGrazia & Daphne Scott
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
Runners-Up: JKZ
Preliminary Concert Winners: October Road • The New Originals • JKZ
Wild Card Picks: Midnight in Montana • The Ska-lers
Standby Bands: Footsie with Suzie • Quantum Entanglement
Grand Finale Emcees: Nicolas DeGrazia & Daphne Scott
More info coming soon...
6th Annual Bitter Jester Music Festival, 2011
Grand Champions: JKZ
Runners-Up: (info coming soon)
Preliminary Concert Winners & Wild Card Pick: JKZ • On the Fly • Specktrum • Erosion • The Burrows 4
Grand Finale Emcees: Nicolas DeGrazia & Daphne Scott
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
Runners-Up: The Aftershow
Preliminary Concert Bands Advancing to Grand Finale: Brownie Mountain • The Aftershow • The Burrows 4 • We’re Not From Utah
Wild Card Pick: Halyard
Grand Finale Emcee: Nicolas DeGrazia
More info coming soon...
4th Annual Bitter Jester Music Festival, 2009
Tied Grand Champions: The Burrows 4 • Maq
Preliminary Concert Winners: Darwin Mingo • Unemployed • Maq • The Burrows 4 (tie) • The Railjacks (tie)
Grand Finale Emcees: Nicolas DeGrazia & Charles Turck with Ariel Univer as “Candy Girl”
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”)
Runners-Up: (info coming soon)
Preliminary Concert Winners: (info coming soon)
Grand Finale Emcee: Nicolas DeGrazia
More info coming soon...
2nd Annual Bitter Jester Music Festival, 2007
Grand Champions: Fat Lisa
Runners-Up: (info coming soon)
Preliminary Concert Winners: (info coming soon)
Grand Finale Emcee: Scott Derenger
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
Runners-Up: (info coming soon)
Preliminary Concert Winners: (info coming soon)
Grand Finale Emcee: Hannibal Buress
More info coming soon...
Pictured to the left: Adam Beck attended the 20th Anniversary of the Bitter Jester Music Festival in 2026 - where he began his musical career as a teenager - to pose with the same exact prize check he won in 2006 along with Festival Founder, Nicolas DeGrazia.
Adam is now the drummer for Sincere Engineer. Check them out on Spotify here!