The Heartbreak Kid may refer to:
Films 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
Other A 1974 song by Bo Donaldson and the Heywoods A 1987 song by Icehouse from their album Man of Colours Nickname of the American professional wrestler Shawn Michaels