The Lucky One

Castleman wrote "The Lucky One" in 1984 at a guitar workshop in Connecticut, and a friend, Buck Brown, made a demo. Around 2000, while he toured with Krauss, he was playing an old cassette and she asked what it was. She changed the song to the second person, where he had sung it in the first, and took no writing credit. He describes it as about a man with a positive outlook who sees the glass half full despite a checkered past.

It is the third track on New Favorite (Rounder, August 14, 2001), 3:10 on the album and 3:06 on the single. It was the first single and the only one of the album's three to chart, reaching number 46 on the country chart. At the 44th Grammy Awards it won best country performance by a duo or group with vocal, and best country song, which goes to the songwriter. A video came out before the single. It is also on Live (2002), played at the Louisville Palace. Our upload carries the album's name, and which version it is was not confirmed.