"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." ==Remix==