2025 Bitter Jester Winners & Musicians of the year

Huge thank you to Highland Park City Council members Annette Lidawer, Yumi Ross, & Andrés Tapia as well as First Bank of Highland Park President Eric Ephraim for joining us at this year’s Grand Finale! First Bank of Highland Park is our Grand Finale Prize Money Title Sponsor. BJMF Co-Host Peter Sagal generously donated his time yet again in support of our nonprofit festival.

Winners are pictured with Humes and Berg drum cases, part of our 2025 “Tour Ready Package” awarded to Grand Champs and Runners-Up!

2025 Grand Champions

Platinum Moon

2025 Runners-Up

Charlieboy

2025 Honorable Mention

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Bitter Jester Music Festival Grand Finale 2025 Co-Hosts, BJMF Founder/Producer Nicolas DeGrazia and Peter Sagal from NPR’s “Wait Wait… Don’t Tell Me!” fame!

2025 Musician of the Year Awards

The Musician of the Year awards at the Bitter Jester Music Fest represent one of the most prestigious honors for talented individual performers in this age range.

Celebrating musical excellence and outstanding performance chops, each recipient is selected by majority vote of our judges and VIPs. They are recognized with a stunning, custom-made “Olympic-style” brass medallion, designed by Christy Knapp and Nic DeGrazia, and produced by Bennett Awards.

These medallions symbolize not just achievement, but also the dedication and passion that musicians bring to their craft. Winning a Musician of the Year award is more than just a trophy; it's a testament to Bitter Jester performers’ hard work, originality, and connection with the audience (judges and patrons alike)!

By participating in BJMF, not only do performers compete for these coveted recognitions, they also gain exposure to industry professionals and a vibrant community of fellow musicians from Chicagoland and beyond. You could be the next Bitter Jester Musician of the Year!