Black Sheep Boy is Okkervil River's third album, released on April 5, 2005. The title is inspired by the song "Black Sheep Boy" by '60s folk singer, Tim Hardin. The album deals with Hardin's struggle with heroin addiction and Sheff's failed relationships and heartbreaks. The album cover features the work of Providence artist William Schaff.
Most of the songs for the new record were written in February 2004 in Bloomington, Indiana by Will Sheff. Sheff describes the album theme in a 2005 interview.
"The Black Sheep Boy is a fantastical character that crops up here and there on the album. In the lyrics pretty much anything in quotes is the voice of the Black Sheep Boy. I think a lot of the dirtier, rougher, more obtuse songs are the product of the Black Sheep Boy."