Loudon Wainwright III Provides a Charlie Poole History Lesson

In the great tradition of folk musicians, Loudon Wainwright III mixes true stories and fictional tales on his latest album, 'High Wide and Handsome: The Charlie Poole Project,' a collection honoring an often overlooked Depression-era singer. On Monday night, Wainwright brought those songs and stories to New York's City Winery, weaving a history lesson into an intimate acoustic concert.

The album, which is in stores now, is a mix of originals and songs that Poole -- who was also a bootlegger, millworker, gambler and amateur baseball player -- covered in his brief career in the '20s and '30s before dying at age 39 after an epic bender. Flanked by David Mansfield (violin, mandolin, slide guitar) and Chaim Tannenbaum (banjo, guitar, harmonica), Wainwright kicked things off with Will Handy's 'Didn't He Ramble' then told the crowd how he first became "hip to" Poole in the early '60s folk boom. He then introduced 'The Deal,' a song he said Poole recorded in 1925, selling 102,000 copies and only making $75 from it, which was split three ways among his band.

Wainwright also took the time to acknowledge the venue, saying "Poole was a terrible drunk who drank himself to death, so it's fitting we're here at City Winery," before launching into 'Goodbye Booze.' He also shared a bit of his own history, introducing 'If I Lose' by saying how he used to play it while busker in London with his ex-wife, Kate McGarrigle, but was forced to stop once the other street musicians found out he had a record deal and threatened to break his thumbs.

Throughout the night, Wainwright also proved to be an excellent salesman, constantly reminding fans that the CD was available now and that he would be signing with it later and posing for camera phone pictures. Asked by a host from radio station WFUV, which was broadcasting the concert live, if he would be indulging in any wine during the show, Wainwright replied "I think I'll stick to water then get roaring drunk before the CD signing party. Come over and I'll vomit on you." He also discussed how having his children, Rufus and Martha Wainwright, on the album was great, as it's always fun for the family to get together in the studio. He then joked that it's the Thanksgiving dinner table that's difficult for the family and their famously strained relationships.

The concert continued with a beautiful rendition of 'The Letter That Never Came,' with Wainwright performing alone on the banjo, an appearance by singer Maggie Roche on 'The Man in the Moon' and a show-stopping three-part harmony on the gospel song 'The Great Reaping Day.' The Poole portion of the concert fittingly ended with the Wainwright original, 'Charlie's Last Song.'

After a loud round of applause, Wainwright returned for an encore and announced to the crowd, "We're not on the radio anymore so I just want to say 's---.'" He then performed his 1972 novelty hit, 'Dead Skunk,' to close out the night. When the song ended, Wainwright got in one last gag, ordering the crowd to "stand up and give me some validation" before he walked off to start his CD signing.