The booklet insert that accompanies Michael McDermott’s latest album, Hey La Hey, features a nostalgic photo of a young couple on what appears to be their wedding day. While no explanation is provided in the credits, to those who’ve seen McDermott in the flesh, the familial resemblance is unmistakable. And though, at first blush, it might seem oddly incongruous with the other images on the disc, the glimpse this photo (of his parents) offers into McDermott’s personal world and (Irish American) heritage serves as a perfect preface to not only Hey La Hey itself, but McDermott’s catalog as a whole, and the life stories – McDermott’s and others – his songs so timelessly capture.

A decade later, that statement continues to apply. McDermott’s father once held a job parking cars “for a Clark Street dive” in Chicago’s Near North Side neighborhood, and it’s his nickname from those days that’s borrowed by the title character in The Ballad of Johnny Diversey, a musical crime caper on Hey La Hey, about which screenwriter Brian Koppelman says, “These are great characters, real and mythical at the same time, and I want to know 'em, to hang with them in that bar, which, from the sound of it, isn't that far from where the good ol' number 49 train rumbles into Chicago.”