Rosie Perez revealed on The Drew Barrymore Show that she played matchmaker between Madonna and Tupac Shakur during the 1993 Soul Train Music Awards. After her original date canceled at the last minute, her friend Tupac offered to accompany her, leading to an unexpected encounter with Madonna, who expressed interest in Shakur. Perez successfully arranged the connection, resulting in a secret romance between Madonna and Tupac that lasted until early 1995. Their relationship was largely private but confirmed by Madonna years later, with a notable letter from Tupac explaining his concerns about their interracial relationship. Despite their split, the impact of their connection remained significant, as highlighted by a song they recorded together that was ultimately unreleased due to controversy. The story reflects the intertwining lives of these iconic figures from the '90s.