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Tess has been a judge since 2021

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Tess Clare

Bitter Jester Music Festival Judge

Honorable Mention (4th Place out of 56) in the 2020 Bitter Jester virtual Original Song Competition

Tess Clare (Tess Considine) began writing, recording and releasing music at the age of 13. As her musicianship progressed, Tess made the decision to finish out her junior and senior year at Interlochen Arts Academy in Traverse City, Michigan.

She has appeared on the radio numerous times with the Bitter Jester Music Festival, playing her music live on-air, and was the Featured Solo Performer at the 2014 Bitter Jester Grand Finale.

“I had such a fun time participating in this festival. I got to be interviewed about my music and I had the chance to meet so many other musicians who were close to my age. At the Grand Finale, there were a couple thousand people there by the end of the night. That experience, as well as playing on WGN and WBEZ radio, gave me great exposure at such a young age.

People even came to my gigs afterwards and told me they did because they heard me on the radio. This really demonstrated how helpful Bitter Jester’s Music Fest is to young, emerging artists.”

-Tess Clare

In 2017, she found her way to Nashville’s Belmont University as a Songwriting Major with a Music Business Minor. During the first day of her Intro to Songwriting class, Tess was asked to perform a song for visiting industry professionals who subsequently signed her to Kontor Records, a German dance label, to release in collaboration with BMG Music Rights. Tess went on to be a finalist in the 2019 Grammy U Showcase in Nashville.

In November 2019, Tess released a pop Christmas single, “Sleigh,” that was immediately added to Spotify Editorial playlist New Music Holiday. “Sleigh” was a great success, particularly as it was her debut independent single as Tess Clare. The song currently has over half a million streams on Spotify and was ranked on Seventeen Magazine’s “12 Best New Christmas Songs of 2019” and numerous other periodicals and blogs chose it for their lists of top Christmas songs.

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Additionally, Bitter Jester Judge Billy Corgan (Smashing Pumpkins) said of “Sleigh” in 2020:

“Tess Clare has a strong voice with international appeal. There is talent here for success.

Confidence always comes across in young artists when they believe.”

-Billy Corgan


Tess’s music has evolved into an organic pop sound. Imagine Ed Sheeran and Adele walk into a bar to have a drink with Maggie Rogers. Amy Winehouse is singing, and they spot Bruce Springsteen across the room. That basically sums it up.

Tess is gearing up for the release of her upcoming EP and is thrilled to return as a Bitter Jester Judge after competing years ago!

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