During a career that’s spanned nearly four decades, singer-songwriter Loudon Wainwright III has produced some of the most idiosyncratically moving songs of his time. (Johnny Cash famously included a live cover of “The Man Who Couldn’t Cry” on his major comeback album American Recordings, to the delight of a hip crowd at LA’s Viper Room.) While most probably know him from his novelty hit “Dead Skunk” off of 1972’s Album III, or from his occasional appearances as the “singing surgeon” on the TV series “M*A*S*H,” Wainwright’s talents as a writer and entertainer run much deeper. Born the son of LIFE magazine editor Loudon Wainwright, Jr., he rebelled against his privileged Westchester County roots, and at the age of 20 he found himself getting bailed out of jail in Oklahoma on a marijuana charge by his Dad, who flew in from London for the proud occasion. In recent years the 1960’s rebel has been increasingly recognized as the father of Canadian-American singer-songwriter Rufus Wainwright, whose mother is musician Kate McGarrigle. Just this summer, Loudon Wainwright III released Strange Weirdos (Concord), which serves as the soundtrack for the movie Knocked Up. It’s a great record that proves his ongoing skill as a lyrical tunesmith and singer with an acute eye focused on life’s funny, sad and profound moments. And if this preview doesn’t include enough info about his family tree, let’s also mention that the show-opener is daughter Lucy (Wainright) Roche, whose Mom is Suzzy Roche, of famous folk-sisters the Roches.

7pm. Tralf Music Hall, 622 Main St. (852-2860/www.tralfmusichall.com). $20 advance

(New World Record, Ticketmaster) or $23 day of show