Robert Lee Castleman (born July 14, 1952) is a Nashville singer-songwriter.
[1]Castleman was attending the birthday party of Alison Krauss, his friend's wife, when nearly all the guests have left. He picked a guitar in view and Krauss requested him to play.
Krauss was impressed by his performance and called her record company Rounder to sign Castleman.
He released his debut album, Crazy as Me, on Rounder Records in August 8th of 2000. The album received positive attention.
At the Grammy Awards in 2002, he won Best Country Song category as the writer of the song "The Lucky One," performed by Alison Krauss & Union Station.[2][3]