"Try Sleeping with a Broken Heart" is the second single by American recording artist Alicia Keys from her fourth studio album, The Element of Freedom, released on 17 November 2009. The ballad, which is a blend of Synthpop and R&B, has been hailed by many music critics as the best track from the album, it marks a departure in Keys' artistic production. The song peaked at #7 on the UK Singles Chart and also reached #27 on the U.S. Billboard Hot 100.