"Try Sleeping with a Broken Heart" is a song performed by American recording artist Alicia Keys. It was released as the second single (third in the UK) from her fourth studio album, The Element of Freedom (2009). The ballad has been hailed by many music critics as the best track from the album. It marks a departure in Keys' artistic production. This single was Keys' third consecutive top 10 hit from The Element of Freedom in the United Kingdom. It was also the 99th most successful song of the year 2010 in the Billboard Hot 100.