Which R&B singer performed the 1999 hit 'Heartbreaker' with Jay-Z?

Which R&B singer performed the 1999 hit “Heartbreaker” with Jay-Z? Mariah Carey did. The song was released as the lead single from Carey’s seventh studio album, Rainbow, and Jay-Z contributed a rap verse.

“Heartbreaker” marked an important step in Carey’s growing blend of pop, R&B, and hip-hop. She had already begun incorporating stronger hip-hop elements into her music on Butterfly, and this collaboration extended that direction. The song’s hook was built around a sample from Stacy Lattisaw’s 1982 song “Attack of the Name Game.”

Released in August 1999, “Heartbreaker” became Carey’s 14th U.S. number-one single and spent two weeks atop the Billboard Hot 100. It also reached number one in Canada and New Zealand. A common mix-up is confusing this collaboration with Carey’s earlier “Fantasy” remix, which featured Ol’ Dirty Bastard rather than Jay-Z. The original music video did not include Jay-Z because of contractual limitations, although a later recut did.