Jessica Risker returns after seven years with a dreamy new album – Chicago Reader

In May 2018, Chicago psych-folk singer-songwriter and licensed counselor Jessica Risker issued her first album under her government name, the sparse and direct I See You Among the Stars. (She’d previously released music as Deadbeat.) In early 2020, Risker started writing and recording a song per month as part of an informal songwriting club with friends. She created enough material in the course of a year to fill out a full-length, though it would take much longer for her to transform her demos into finished tracks. Ten of those tracks appear on the album Calendar Year, which New York label Island House Recordings will release on Friday, August 1.

Risker’s friend Shelby Turner, who performs as Richard Album, started those songwriter meetups. “We’d get together, share new songs, give each other feedback—it was a casual, fun thing that we did,” Risker says. “Then the pandemic and lockdown started. We continued it, over Zoom—we used to meet in person. We had a monthly schedule at that point. It was this outlet to connect with friends and to keep up with the creativity, in the midst of all that was going on.”

Risker’s demos from the songwriters’ group were bare-bones. She’d record herself singing and playing guitar and flute. Occasionally her son, who was two years old in 2020, would yell in the background. Risker sings about motherhood throughout Calendar Year, and balancing its responsibilities against the demands of her career has created new challenges for her creative life. “I personally really respond well, creatively, to structure,” she says. “So having the structure of the songwriting club—where I knew there was a date, and I knew there was a group that was gonna listen to it—was very helpful. Similarly, having a kid, you gotta map out your day a little bit more thoughtfully and intentionally. That’s not a bad thing; that’s workable.”

To refashion those demos into the baroque, dreamy sounds of Calendar Year, Risker recruited a coterie of musicians. Longtime collaborator Joshua Wentz contributed synths and electronics, Brian Weza played bass, and Steve Plock drummed. Risker couldn’t sing and play flute at the same time, of course, and instead of overdubbing those parts herself, she brought in Fran bandleader Maria Jacobson on flute. To capture the music’s gauzy atmospherics and casual mood, Risker tapped in-demand engineer Dave Vettraino of Public House Sound Recordings, who’d also recorded and mixed I See You Among the Stars. 

Risker will celebrate Calendar Year by headlining Constellation on Friday, September 5; V.V. Lightbody opens.

^{Jessica Risker’s Calendar Year also includes appearances by Macie Stewart and Sam Cantor.}

Trumpeter, composer, and producer Will Miller, who plays horns with the band Whitney, also has a promising career making jazz fusion under the name Resavoir. In May, International Anthem issued Horizon, Resavoir’s collaborative album with jazz guitarist Matt Gold. The richness of Miller’s style makes it feel huge despite its subtlety, and Gossip Wolf is especially excited to note that Miller’s headlining set at Millennium Park’s Pritzker Pavilion on Monday, August 4, will feature the reassembled Orchestra Resavoir—a superlatively large and lush version of the group! Orchestra Resavoir most recently played at Thalia Hall in December 2024, when Miller brought along 15 seasoned musicians to flesh out his sound. Saxophonist Isaiah Collier opens the show, and DJs Sonny Daze and King Hippo spin between sets. The free concert starts at 6:30 PM.

^{Will Miller and Matt Gold are joined by as many as six other players on Horizon.}

This past weekend, Grunts Rare Books in Douglass Park (1500 S. Western, suite 403) announced a weekly music series called Grunt’s Radio. Every Saturday afternoon, Grunts will use a radio in the bookshop to fill the space with new, unreleased, or long-form work by Chicago musicians and sound artists. The series is curated by a local experimental musician who’s already incorporated radio broadcasts into her output: cellist Lia Kohl. She’s also the first featured artist on Grunt’s Radio, which will run Saturdays from 1 PM to 4 PM.

^{Rattle Sharp Candy is one of many outlets for multi-instrumentalist Joshua Rush Crawford.}

If you search Bandcamp using the “Chicago” tag, you’ve almost certainly seen a torrent of releases by local multi-instrumentalist Joshua Rush Crawford. He records cracked egg punk as Elastic People, lo-fi synth punk as the Slags, and lots more. Sometimes he sounds like a carny who’s seen too much, playing a sort of outre punk take on merry-go-round music. About a week ago, Crawford dropped an album called Sticky Sam by yet another project, Rattle Sharp Candy, whose occasionally spooky songs demonstrate his ear for a rad hook.

^{Jack Riedy recorded most of Raw Deal himself, but onstage he plays with a full band.}

Readers of the Reader’s music coverage should recognize the name Jack Riedy: He’s been publishing terrific, out-of-the-box stories about Chicago music in this very paper since 2018. Riedy is not only a talented writer but also a musician with a keen ear for irreverent indie pop. His March album, Raw Deal, lassos together rubbery funk bass lines, leaping jabs of ska guitar, and effervescent keys into unexpected arrangements that animate Riedy’s rambunctious melodies. On Saturday, August 2, Riedy and his backing band, the Dealbreakers, headline the downstairs space at Subterranean; Oux and Jon E. Keez open. Tickets cost $17.78 in advance, and the show starts at 7:30 PM.