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Jill Sobule’s acoustic one-woman show at the City Winery July 31 promised to be a quiet intimate, evening but turned out to be a spectacular packed with surprise guests, high and low comedy, and a hearty helping of warm fuzzy queer cheer.

The tip-off was in having award-winning singer-songwriter and Chicago Force quarterback Sami Grisafe as the opener. With longtime friend Linsea Waugh joining her on guitar and vocals, Grisafe performed songs from her recent Atlantis CD (Vicious Muse Records). Grisafe and Waugh alternated vocals then joined in firm but lithe harmonies on “When I think of You,” “Two of Hearts” and the bouncy “Hooky (in Chicago).”

With Grisafe setting the bar so high, Sobule grabbed the baton and ran with it. Promoting her new Dottie’s Charms CD (Pinko Records), Sobule joyfully set the tone for the night by announcing early on, “I’m working without a set list here.”

Her reading of the David Bowie/Mott the Hoople chestnut “All the Young Dudes” was an indication that she had all kinds of treats tucked away for the evening. “Where Is Bobbie Gentry?,” “My Chair” and “I Hate Horses” came sandwiched between anecdotes and jokes about the rock band Kansas (a running gag had Sobule constantly playing the Intro to “Dust in the Wind”), Katy Perry, Bobbie Gentry and Chicago weather.

Local out legend Cathy Richardson joined Sobule onstage for a giggly rip through “Kissed A Girl,” while Grisafe and Waugh joined her to sing the nights biggest joke, a song titled “This Song Is Boring.”