The Heartbreak Kid may refer to:

• The Heartbreak Kid (1972 film), an American film starring Charles Grodin and Cybill Shepherd
• The Heartbreak Kid (1993 film), an Australian film starring Claudia Karvan and Alex Dimitriades
• The Heartbreak Kid (2007 film), an American film starring Ben Stiller and Malin Akerman

• A 1974 song by Bo Donaldson and the Heywoods
• A 1987 song by Icehouse from their album Man of Colours
• Ring-name of the American professional wrestler Shawn Michaels, from 1992 onwards.