Sep 3, 2026 10:44 AM
In Memoriam: Cassandra Wilson, 1955–2026
Cassandra Wilson, a singer, songwriter and producer who was one of the most acclaimed and successful jazz vocalists of…
Madeleine Peyroux onstage in Chicago on April 5 (Photo: Michael Jackson)
(Photo: )Madeleine Peyroux does not sing like Billie Holiday. Critics have often compared her to Lady Day, but in the first of two shows on April 5 at Chicago’s Old Town School of Folk Music, the singer-songwriter proved that onstage, the only artist she sounds like is Madeleine Peyroux.
She grew up listening to a lot of Holiday records, and Peyroux’s phrasing sporadically echoes that of the icon, but comparisons between the two singers have carried less significance as the Georgia native’s career has evolved during the years since her debut disc, 1996’s Dreamland. Still, the comparisons will persist, partially because Peyroux sometimes includes in her concerts tunes that Holiday recorded, such as “I Hear Music.”
Peyroux’s 14-song set included eight numbers from her excellent new Decca album, The Blue Room. Her supple alto was framed by an agile octet that included her core band—guitarist Jon Herington, keyboardist Gary Versace, bassist Barak Mori, drummer Darren Beckett and violinist Sylvia D’Avanzo—as well as cellist Jared Snyder and violinists Margot Schwartz and Eric Segnitz.
Peyroux occasionally strummed an acoustic guitar during the 68-minute concert, but she was more effective without it. Standing in front of a microphone stand, she rocked back on her heels and flexed on her toes, two examples of how she can use her entire body to help extend a melancholy note.
The Blue Room, released in March, is centered on interpretations of songs that Ray Charles recorded on his 1962 LP Modern Sounds In Country And Western Music and its Vol. 2 followup. In Chicago, two of those tunes showcased the virtuosity of Versace, who alternated between piano, organ and electronic keyboard throughout the show.
On “Born To Lose,” Versace’s gorgeous piano lines sparkled against Beckett’s hushed brushwork, while on “I Can’t Stop Loving You,” he coaxed chords from the organ that reinforced the yearning message of the song’s lyrics.
In the introduction to her tear-jerking rendition of “Born To Lose,” Peyroux told the crowd, “First, we’re going to break your heart, and then we’re going to cheer you up.”
Cheerfulness isn’t the first concept that comes to mind when pondering Peyroux’s oeuvre, but she delighted the crowd with her elastic phrasing in a swaying version of the Buddy Holly tune “Changing All Those Changes.”
Her Old Town School set list also included exquisite versions of songs by Bob Dylan (“You’re Gonna Make Me Lonesome When You Go”) and Leonard Cohen (“Bird On The Wire,” “Dance Me To The End Of Love”). Singing material by those tunesmiths for a crowd in this venue was a proverbial case of preaching to the (midnight) choir. Peyroux easily could have coasted, but the nuance of her sculpted delivery made these versions compelling.
Peyroux closed the show with Warren Zevon’s “Desperados Under The Eaves,” offering an arrangement that transformed what could have been a stumbling block—the song’s hummed section—into an exercise in cinematic, emotional storytelling.
—Bobby Reed
Wilson’s ability to connect to audiences helped her to win two Grammy awards and multiple other accolades. She was named an NEA Jazz Master in 2022.
Sep 3, 2026 10:44 AM
Cassandra Wilson, a singer, songwriter and producer who was one of the most acclaimed and successful jazz vocalists of…
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