Sleepless Nights is the fifteenth album by American country music artist Patty Loveless. The album was released on September 9, 2008 (see 2008 in country music). Her first album for the Sagauaro 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.

Allmusic critic Thom Jurek gave Sleepless Nights a four-star rating out of five, saying "Loveless takes each of these cuts deep into the well of her heart and let's [sic] them rip." Jurek also said that Emory Gordy, Jr., Loveless' husband and producer, "showers [the songs] in emotion and Loveless simply needs to open her mouth to tell the story behind the words to get it across to the listener, where it resonates deeply."