There's a squirmingly funny scene in Judd Apatows TV series, Undeclared, in which Loudon Wainwright III offers to play a song for Adam Sandler, who is visiting Wainwright's son's dorm. Instead of singing some quaint tune, Loudon brays an angry number directed at his wayward wife: "Dumpin' me's a crime/You're runnin' out of time/You're way past your prime/You'll never find a man." For 30-plus years, Wainwright has been concocting similarly surprising tunes, offering a plethora of juvenile wit, biting sarcasm, and keen insight into the human condition. His latest disc, Strange Weirdos, includes music used in and inspired by Apatow's recent movie hit, Knocked Up, and is his finest in ages. Whether penning jaunty odes to parental indecision ("X or Y") or the rush of new love ("So Much to Do"), Wainwright sounds as enthusiastically bewildered as he did back in 1970. Co-writer Joe Henry, guitarist Richard Thompson, and arranger Van Dyke Parks add to the vibrant arrangements, but, as always, Wainwright's lyrics take center stage. On "Final Frontier," the New York native cements his reputation as the poet laureate of confounded males, singing, "I thought that I had it, but I was just in it/It became a battle, I could never win it/Each time I won it, I could never keep it/When called on to say it, I could never speak it." It's small wonder that he's friendly enough with his exes that he can perform with them, as he does with Suzzy Roche tonight.
Sun., Nov. 18, 8 p.m., 2007