What would happen if Emmylou Harris went through the looking glass? The effect might be a lot like Chicago-based Americana alt-country artist Michelle Billingsley, welcomed to the A2SF Rackham Stage this summer. With charmingly cutting lyrics wrapped in boisterous acoustic strumming, a dry sense of humor, and whip smart vocal delivery, Billingsley’s music is irreverent and fearless in the same breath, Nancy Sinatra’s swagger tempered with the straightforward edge of Neko Case. Her debut album, Not the Marrying Kind, presents a spare yet moody vibe, deceptively heavy but undeniably fun. Brilliant whimsy, black comedy, brisk melodies – Billingsley combines all these elements to produce music that is all too human and deeply affecting.