"How Do You Sleep?" is the third single from Jesse McCartney's third studio album, Departure. The song was released on January 20, 2009. "How Do You Sleep?" received favorable reviews. Billboard gave the song a positive review: "While his previous single 'It's Over' failed to achieve the same success as his No. 1 top 40 hit 'Leavin',' Jesse McCartney keeps the ball rolling with 'How Do You Sleep?' from his 2008 CD Departure. He croons about his lost love, 'It's been about a year now/ Ain't seen or heard from you/Been missing you crazy,' to a twangin' hip-hop beat co-penned and co-produced by R&B master Sean Garrett. R&B and rhythmic stations smart enough to embrace Justin Timberlake would be wise to indulge another white boy, who fuels the fire with remixes featuring Ludacris. McCartney has certainly grown up; now it's time that radio gave this talent his just deserts: sustained stardom." About.com stated, "The beats here give an insistent atmosphere that will make 'How Do You Sleep?' hard to forget and added that with raps from Ludacris adds a great muscular addition to the song."