Gary Jules ( born March 19 , 1969 ) is an singer and his song , `` Mad World '' was played in the film , Donnie Darko . Gary Jules ( born March 19 , 1969 as Gary Jules Aguirre , Jr. ) is an American singer-songwriter , best known for his cover of Tears for Fears ' third single `` Mad World '' , which he recorded together with friend Michael Andrews for the film Donnie Darko .