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It’s a good thing Loudon Wainwright’s Older Than My Old Man Now is so funny, because otherwise it would be unbearably sad. Older Than My Old Man Now is a concept album about death and decay that posits the inexorable march of time and the inevitable embrace of the grave as two-thirds raucous comedy and one-third tragedy. It’s an album about endings: of sex, of life, of hope, of families, and most mercifully, old grudges and grievances so powerful they can outlast life if given a chance.
Wainwright is the patriarch of one of pop music’s most brilliant and troubled dynasties, a sort of real-life version of Wes Anderson’s Tenenbaums or J.D. Salinger’s Glass family. The album’s most achingly sad moments delve—with clear-eyed, unblinking candor—into lingering, age-old pain of an unmistakably familial variety. Part of what makes Older so resonant and poignantly voyeuristic is the pervasive sense, real or not, that Wainwright can reach his children through music in a way that he can’t any other way. When he sings with son Rufus on the haunting “The Days That We Die” or Lucy on the funny-sad “All In A Family” (whose contention “What family is not insane?” may be the key line on the album), he’s connecting with them as artists in a way he never could as a terribly flawed father. It’s an exquisitely bittersweet meander through Wainwright’s cobweb-strewn psyche liable to leave listeners laughing through tears and crying through laughter. — A.V. Club