The contract covers Jay-Z's music and music-related businesses for the next 10 years, the New York Times and Wall Street Journal reported on their Web sites late Wednesday, citing sources familiar with the agreement.
An after-hours call to a Live Nation spokesman seeking comment was not immediately returned late Wednesday.
Live Nation was also expected to commit $50 million to finance Jay-Z's investments and his entertainment venture, to be called Roc Nation, which is expected to include his own record label, music publishing, talent consulting and managing projects.
"I've turned into the Rolling Stones of hip-hop," Jay-Z told the Times.
Jay-Z, whose real name is Shawn Carter, plans to leave Def Jam for the deal, but he still owes his longtime record label one more studio album.
He was president of Def Jam for three years but stepped down in December because he and the label's corporate parent, Universal Music Group, could not agree on a new contract.
Live Nation also struck recent deals with Madonna and U2.