Which rapper has the most Grammys? 24-time Grammy Award winner Jay-Z. Jay-Z and Kanye West, each with 24 awards, have won more Grammy Awards than any other rapper. Lauryn Hill is the most awarded female rapper, with eight Grammy Awards. In 1998 Jay Z released his breakthrough album, Vol. 2 … Hard Knock Life, which went to No. 1 on the Billboard 200 and spawned the Top 20 mainstream hit, “Can I Get A …” Jay Z took home his first GRAMMY for Best Rap Album for Vol. 2 … Hard Knock Life for 1998. Currently tied with Kanye West, Jay Z holds the distinction of rapper with the most GRAMMY wins in history. He made his GRAMMY performance debut at the 48th GRAMMY Awards in 2006 when he teamed with Linkin Park and Paul McCartney for a medley of “Numb/Encore” and “Yesterday.” Former President Barack Obama named Jay Z as one of his favorite rappers along with Kendrick Lamar, Chance The Rapper and Drake. Did you know? The Recording Academy New York Chapter honored Jay Z, Mariah Carey, Yoko Ono and John Lennon, and film composer Howard Shore as 2005 recipients of The Recording Academy Honors. Jay Z and his mother, Gloria Carter, established the Shawn Carter Foundation in 2003 to help individuals facing socio-economic hardships and empower youth and communities in need through a scholarship fund, college tours, study abroad experiences, counseling initiatives, and giveback programs.