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Sound check: Bitter Jester song contest, Deanie Boy debut, new When the Sun Sets EP

Bitter Jester lives on

The Bitter Jester Music Festival, Highland Park's annual summerlong concert series, had to be canceled under social distancing requirements and concerns about the COVID-19 pandemic. But festival organizer Nicolas DeGrazia wasn't about to sit around tuneless all summer. Bitter Jester announced last week that this summer's series will be replaced by a virtual original songwriting contest, open to any band as long as more than half of the members are younger than 21. Two winning songs will be selected by a panel of judges, along with a fan-favorite song selected over social media. For more information or to enter (before May 31, please!), visit bitterjesterfoundation.org.

Fresh tracks

• Dean Sinclair is a man of action. The drummer for indie pop band August Hotel also plays with Capital Soiree and The Mackenzie O'Brien Band and fronts Deanie Boy. Wait, what's this Deanie Boy? As one of the songwriters for August Hotel, Sinclair, who grew up in McHenry, is well-versed in putting his thoughts and ideas out there through somebody else's voice, somebody else's delivery. But this seemed like the perfect time to tackle a long-simmering challenge: fronting his own songs. “I just kind of figured it'd be cool or fun for me to sing what I actually wrote. That's something that I've never done before. I've never performed or recorded myself really singing in front of anybody before. It's always been something I've been a little insecure about it, but I just thought, why not?” Enlisting the help of Ember Oceans' Freddy Purcell and Steven Rejdukowski of Capital Soiree for guitar, bass and engineering help, Sinclair readied Deanie Boy's debut singles — “New York” and “Your Side” are two pop-soaked tracks that will breathe fresh air into this spring's playlists — for Friday's release. Hear the tracks and read our full interview with Sinclair at chicagosoundcheck.com.

• Zack Baumgartner and the Huntley-based pop-punksters When the Sun Sets are on the verge of dropping “Transparent,” the band's newest EP. Baumgartner's focus since it started has been to reach out to people, to be clear about his own struggles and to help others with their own. “The record being named ‘Transparent,' that's exactly what we want to do with our audience. ... To make the listener feel like they're not alone if they're going through the same type of stuff. They know exactly who their music is coming from ... It's genuinely more showing them who we are.” The 7-song EP is out on all major streaming services Friday. Hear it (and read our full interview) at chicagosoundcheck.com.

• Brian Shamie is a Daily Herald multiplatform editor and local music junkie. Email him at bshamie@dailyherald.com, find him on Facebook or follow him on Twitter (@thatshamieguy) or Instagram (@chicagosoundcheck). Brian also keeps tabs on the Chicago-area music scene at chicagosoundcheck.com.

Courtesy of Alex ZarekWhen the Sun Sets releases its 7-song collection of pop-punk tunes, "Transparent," on major streaming services Friday, May 8.
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