Music series

Bitter Jester is gearing up for the Highland Park musical series this week

Highland Park’s Bitter Jester Music Festival is counting down to the opening act of its four-week showcase series, which begins its 16th season this weekend.

The weekly competition series kicks off at 6:30 p.m. on Friday, May 20, with six up-and-coming Midwestern artists performing live at Madame Zuzu’s (1876 First St., Highland Park), the tea house and concert venue owned by Smashing The Pumpkin Singer. Billy Corgan.

The contest will be hosted by Emmy-winning writer, producer and director and Bitter Jester founder Nicolas DeGrazia. The contestants will perform each week in front of a fresh roster of music industry professionals, who will offer feedback and new perspectives to the musicians.

Two guest showcase artists and a guest performer will complete each evening.

The contest continues the following three Fridays at Bitter Jester’s usual outdoor home in Port Clinton Square (600 Central Ave., Highland Park), with new acts each week. Performances are free. Judy’s Pizza and Sweet Home Gelato will be on hand, so guests can grab dinner and drinks with the shows.

Here is the program :

Friday May 20

From 6:30 p.m. at Madame Zuzu

• Joey Wilbur

• Kanin Elizabeth

• Keep the eleven


• New Age Americans

• What we once had

Showcase performers: Private School, Sparky

Guest artist: Jordyn Andrea

Friday May 27

6:30 p.m. at Port Clinton Square


• Chainsaw Boyz

• David’s house


• Imperial Orange

• Burnt waves

• You understood the message

Featured Artists: Flannel Folk, Vegan Steakhouse

Guest artist: Claire-McKenna

Friday, June 3

6:30 p.m. at Port Clinton Square

• Divider

• Fight Bob

• Fluctuation

• Ian Jake Robleza

• Jagger

• Opening day

Star performers: The Dennies, Sara Pilkati

Guest Artist: Madeline O’Dell

friday june 10

6:30 p.m. at Port Clinton Square

• Linda Therese

• Nyx

• Rae

• Summer driving

• Summer League

• Revenge

Featured Artists: This Violet Hour, Jabari Zakee

Guest artist: Kate Larson

The Bitter Jester Music Fest returns for its 16th season in Highland Park, starting with a concert and competition on Friday, May 20.
– Courtesy of Bitter Jester

Select Bitter Jester contestants will be invited to perform at 5 p.m. Thursday, June 23 at Ravinia Festival.

The Grand Finals concert – starting at 3:45pm on Monday July 4 – will highlight the finalists vying for the Grand Champion title and prizes. The event will take place at Wolters Field, 1080 Park Ave. West, Highland Park, and culminates in the Town of Highland Park Independence Day Fireworks Show.

To visit for details on each week’s groups, judges and contest prizes.