On February 8, 2009, the album won all five awards for which it was nominated at the 51st Grammy Awards: Album of the Year; Best Contemporary Folk/Americana Album; Record of the Year (for "Please Read the Letter"); Best Pop Collaboration with Vocals (for "Rich Woman"); and Best Country Collaboration with Vocals (for "Killing the Blues").
On February 8, 2009, the album won all five awards for which it was nominated at the 51st Grammy Awards: Album of the Year; Best Contemporary Folk/Americana Album; Record of the Year (for «Please Read the Letter»); Best Pop Collaboration with Vocals (for «Rich Woman»); and Best Country Collaboration with Vocals (for «Killing the Blues»).