Born: 1946 in Chapel Hill, N.C.
Sounds like: Steve Martin playing a banjo concert at a Delaware prep school.
For fans of: Pete Seeger, Bob Seger, Richard Thompson, Kate McGarrigle, Rufus and Martha Wainwright, Seth Rogen.
Latest release: 10 Songs for the New Depression (2010).
Why you care: Despite being nominated as a "new Bob Dylan" (what singer-songwriter from the '70s wasn't?), Loudon Wainwright never dove headfirst into fame; instead, he keeps dipping his toes in the pool. One of his silliest songs, "Dead Skunk," became a novelty hit in 1972; he had a recurring role as a singing surgeon on television's M*A*S*H; his transcendent "Swimming Song" graces the closing credits of The Squid and the Whale; Judd Apatow cast him as an obstetrician in Knocked Up and as a hapless dad on Undeclared. The latter role, a comic mirror of his own fraught relationship with children Rufus and Martha, hints at Wainwright's penchant for announcing his failings and hymning his selfishness. He puts real guilt back into confessional songwriting: What other performer could croon about smacking his child ("Hitting You"), engaging in barely functional alcoholism with his mother ("White Winos") or refusing to see another child ("A Year")? Perhaps as a kind of penance, Wainwright's kids have become more famous than he is; Martha lets him appear with her onstage, but also calls him a "bloody motherfucking asshole" in a song title. I can't blame them for their reservations, but I embrace the old man wholeheartedly.
Loudon Wainwright III plays the Aladdin Theater on Monday, Jan. 24. 8 pm. $25. All ages (minors must be accompanied by a parent).