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The Singer and The Song features three full sets of music for dancing, drinking and listening, with the exciting bonus of a new song from each band, written from a word prompt given in advance.
The artists also pay tribute to Chicago’s music roots by covering a song by another local artist, present or past.
At its heart, this series is a showcase for the incredible songwriting talent of the Chicago music scene, with an emphasis on Country, but including the broadest definitions of Americana.
The monthly event is often hosted by the show’s curators; Brandon Good, Lawrence Peters, and Matt Gandurski, each a key player in Chicago’s music community.
Allegra Malone
https://www.facebook.com/allegra.malone/
The space between genres, where the only tangible is the power of music, that’s where you find Allegra.
Performing began in the Epiphany Gospel choir inBirmingham, and later evolved into a love for the guitar and all things rock and roll after a move to Seattle in her teens.
A perfect hybrid of writer and performer, Allegra finds inspiration in roots music and has come full circle since her move to Chicago from NYC, after singing backup for the notorious Lynne Jordan.
As an original artist, she has become a torchy fixture in the throwback country scene of Chicago, sharing bills with Robbie Fulks, Nora O’Connor and The Henhouse Prowlers, to name a few.
Known as the “Hoyle sister” of the beloved Chicago honky tonk heroes The Hoyle Brothers, she can be seen playing locally at The House of Blues, Fitzgerald’s Nightclub and The Hideout, while recording her debut full band album at FAME Studios in Muscle Shoals, Alabama, due for release in fall of 2026.
Dennis J. Leise and Tiny Horse
https://dennisjleise.bandcamp.com/
Dennis hails originally from Western PA, but for the last 25 years has called the Chicago area his home. He carries the baggage of his rural upbringing, small-town angst, suburban-cultural-wasteland boredom, big-city wit/savvy and current post-apocalyptic confines of Unincorporated Gary, Indiana to life in his songs that are borne, not from situations, but from ideas, practically ensuring his commercial obscurity. His band, Tiny Horse, includes the exceptional talents of Brian Wilkie on guitar and Dan Kristan on Upright Bass.
Wild Western Avenue
https://wildwesternave.com/music
Wild Western Avenue is a Chicago-based outfit that unites classic country, traditional jazz, western swing, jug band, and folk music to create a genre self-described as “cowboy jazz.”
The five-piece formed over the course of a year after frontman Scott Cary moved to Chicago in 2023. Most members met at the Banjo After Dark old-time jam on the city’s north side.
Their influences include Leon Redbone, Bob Dylan, Willie Nelson, John Prine, and Bob Wills, among other classic country greats. During one of their sets, you might hear a Hank Williams cover, a countrified jazz standard, or one of several original songs.
Though the group’s lineup is fluid, core members include Cary (lead vocalist), Kevin Doyle (bass), Chelsea Dvorchak (viola), Elliott Esparza (lead guitar), and Matt Uribe (violin). They’re currently working on their first EP while playing shows across the Midwest.