Wryly incisive throughout his career, perpetually perturbed singer-songwriter Loudon Wainwright III has never shied from loneliness and loss–and there’s plenty of both to go around on the new Last Man on Earth (Red House), which displays his keen sensitivity to the realities and fears of middle age. Wainwright turned 55 this year, and he’s become modern music’s answer to John Updike. He closes this short, sweet album with “Homeless,” a song that addresses his mother’s 1997 death: “When you were alive / I was never alone / Somewhere in the world / There was something called home.” And on the way there, Wainwright describes postbreakup life (“Living Alone”), lapsed friendships (“Out of Reach”), and a preoccupation with mortality (“Donations” includes the lines “As for my corneas / I don’t care who gets them / But all other organs / And parts are for you”). In the album’s strongest statement, “Surviving Twin,” he lays bare the oedipal combination of respect and enmity he felt for his imposing father, who was a well-known columnist for Life magazine. In other words, he’s a long way from the weirdly sarcastic little ditties about bell-bottoms and run-over skunks that characterized his first three or four discs, back in the early 70s. But other elements from those early records remain intact–his lilting folk melodies, his youthful-sounding adenoidal twang, his ear for a memorable phrase–and they complement darker subjects just as effectively. Wainwright also has a talent for incorporating period-specific references that can stand the test of time: I doubt anyone 50 years from now will have trouble parsing “the Pinter pause” he mentions in “Out of Reach,” or relishing the title track’s allusions to trigger locks, computer illiteracy, and the stock-market boom. I may be a bit biased, since last month I turned 50 myself, but Wainwright’s autumnal wisdom makes me smile in recognition, or even laugh in resignation–and it comes bundled up in hummable songs and eminently quotable lyrics. Sunday, October 28, 7 and 9 PM, Old Town School of Folk Music, 4544 N. Lincoln; 773-728-6000.

Art accompanying story in printed newspaper (not available in this archive): photo/Irene Young.