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In the 40-odd years of his career to date, Loudon Wainwright III has had one bona fide hit song (“Dead Skunk,’’ which topped out at No. 16 on the Billboard “Hot 100’’ chart in 1973). A handful of others have been covered by heroes of his (Johnny Cash did “The Man Who Couldn’t Cry,’’ Mose Allison “I’m Alright’’), his first wife and his sister-in-law, Kate and Anna McGarrigle (“The Swimming Song’’), his son, Rufus Wainwright (“One Man Guy’’), and his daughter Martha Wainwright (“Pretty Good Day’’). He’s done some acting (the TV shows “M*A*S*H’’ and “Undeclared,’’ such films as “The 40-Year-Old Virgin’’ and “Knocked Up’’), and fathered three successful professional musicians (Lucy Wainwright Roche, his daughter by Suzzy Roche, is the third).
But what Wainwright ought to be famous for is his excellence as a singer-songwriter. Now the director of “Undeclared’’ and those above-mentioned films, Judd Apatow, has done something about it, co-producing “40 Odd Years,’’ a five-disc box set celebrating Wainwright’s music. Wainwright’s work is typically confessional and self-deprecating. It is usually funny, or poignant, and often some combination of the two. Adult wordplay abounds: “I remember those coming out parties,’’ he sings in “Westchester County,’’ “Where us country-club kids had our fun/ Steal a kiss, cop a feel, off a girl in high-heels.’’
The three principal CDs here consist of songs Wainwright culled from his 24 previous albums. “I was the ‘decider’ on what was included in this box set,’’ he writes in the 40 pages of album notes, “so if your favorite songs of mine were left off, you can blame me.’’ Aside from his own takes on everything named above, the 68 songs making the cut include gems for his father, the journalist Loudon Wainwright II (“Surviving Twin’’), mother (“White Winos’’), and kids (“Dilated to Meet You,’’ “Your Mother and I’’); on fatherhood (“Bein’ a Dad’’), breakups (“Unhappy Anniversary,’’ “Whatever Happened to Us?’’), and a philandering musician (“Motel Blues’’); a pair from the “Knocked Up’’ soundtrack (“Daughter,’’ “Grey in L.A.’’); and three more from his recent Grammy-winning album, “High Wide & Handsome: The Charlie Poole Project.’’
A fourth CD of rare and unreleased tracks includes a homemade one with Kate McGarrigle from before their unhappy marriage. Disc five is a DVD with more than three hours of footage from TV performances and an insightful 1993 Dutch documentary, “One Man Guy.’’ It includes other strong songs left off of the three main discs and elucidates how so many of Wainwright’s songs are rooted in real-life marital, filial, and parental struggles. “Now,’’ writes Apatow, “when anyone I meet tells me they are not that familiar with the work of the great Loudon Wainwright, I can slip them this box and say, ‘Enjoy.’ ’’
Bill Beuttler can be reached at bill@billbeuttler.com. 
© Copyright 2011 Globe Newspaper Company.
