Loudon’s 2CD set and book set from 2009 is tribute to singer and banjo picker Charlie Poole. It features 30 tracks, including new versions of songs made popular by Poole from 1925 through 1930, as well as original songs on Poole's turbulent life by Loudon and producer Dick Connette. It won a well-deserved Grammy Award. Wainwright recalls having first heard of Poole in the early 1970s through folksinger Patrick Sky. Over the next few years, he learned other songs by the North Carolina picker, becoming intrigued by stories of Poole's life and the alcoholism that led to his early death. Loudon initially thought of writing a biographical film on Poole’s life but instead he and Connette collaborated in these recordings. Contributors to the album include his children Rufus Wainwright, Martha Wainwright and Lucy Wainwright Roche; Sloan Wainwright; Maggie, Suzzy and Terre Roche of The Roches; Gabriel Kahane on piano, along with Chris Thile, Geoff Muldaur, David Mansfield, Chaim Tannenbaum and more.

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