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 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." Matt C., a critic for Engine 145, also gave the album a four-out-of-five rating. He described
Sleepless Nights as "a thoroughly arresting listening experience, as Loveless lays twenty-first century gloss, if not sensibilities, on a few songs that haven’t been dusted off in quite some time." Although he criticized the album's lack of up-tempo songs and felt that some of the covers were "uncomfortable", he nonetheless commended Loveless for "find[ing] her wheelhouse on songs that are no-less classic but nonetheless haven’t achieved corner bar ubiquity", also saying "The success of these songs is equal testament to Loveless’ outstanding country voice and the timeless quality of the material she’s selected."
Slant Magazine critic Jonathan Keefe also criticized the album for its lack up-tempo material, but gave it four-and-a-half stars out of five, saying "Loveless has offered another unqualified masterpiece with
Sleepless Nights and reasserted her place as one of the premier artists not just of the country genre but of contemporary popular music."
Sleepless Nights received a nomination for
Best Country Album at the
51st Annual Grammy Awards. ==Track listing==