Sleepless Nights is the fifteenth album by American country music artist Patty Loveless. The album was released on September 9, 2008. Her first album for the Saguaro Road Records label, it is also her first studio album since Dreamin' My Dreams in 2005. Sleepless Nights comprises cover versions of traditional classic country music songs. "Why Baby Why", a song originally recorded by George Jones which has also been a chart hit for several other artists, was released in September 2008 as the first single from the album.

Patty Loveless is an American country music singer. She began performing in her teenaged years before signing her first recording contract with MCA Records' Nashville division in 1985. While her first few releases were unsuccessful, she broke through by decade's end with a cover of George Jones's "If My Heart Had Windows". Loveless issued five albums on MCA before moving to Epic Records in 1993, where she released nine more albums. Four of her albums—Honky Tonk Angel, Only What I Feel, When Fallen Angels Fly, and The Trouble with the Truth—are certified platinum in the United States. Loveless has charted 44 singles on the Billboard Hot Country Songs charts, including five which reached number one: "Timber, I'm Falling in Love", "Chains", "Blame It on Your Heart", "You Can Feel Bad", and "Lonely Too Long".