Though he hasn’t put out a new record since 1998’s Walk Between the Raindrops (whose advice-to-a-teen title track should rightfully appear every May as a graduation gift alongside that damn Dr. Seuss book), James McMurtry’s fans are usually just as content to hear his rich story-song back catalog one more time. His literary tales of drunkards, strugglers, losers and dreamers — all delivered in his trademark drawling monotone — make him the Raymond Carver (and occasionally Charles Bukowski) of Texas singer-songwriters. “Some of these characters are based on people I meet,” McMurtry once said. “There’s whole bars full of them. It’s really disturbing.”

Bob Ruggiero has been writing about music, books, visual arts and entertainment for the Houston Press since 1997, with an emphasis on Classic Rock. He used to have an incredible and luxurious mullet in...