In 1999, Jay Z dueted with Mariah Carey on a song called 'Heartbreaker'. This image appears in the gallery:44 Awesome JAY-Z Facts That Will Blow Your Mind 36. In 1999, Jay Z dueted with Mariah Carey on a song called 'Heartbreaker'. 44 images See the full gallery: 44 Awesome JAY-Z Facts That Will Blow Your Mind