Hip-Hop Awards Milestones: Kendrick Lamar’s Grammy Sweep, Eminem’s Oscar Win & More
Kendrick Lamar made history at the 67th annual Grammy Awards on Sunday (Feb. 2), becoming the first hip-hop artist to win five Grammys more than once. He also became the first artist from any genre to win best music video three times.
Lamar won all five of his 2025 Grammys – record and song of the year, best rap song, best rap performance and best music video – for “Not Like Us.” That incendiary smash became just the second hip-hop hit to win either record or song of the year, following Childish Gambino’s “This Is America,” which also won both awards.
Lamar first won five Grammys at the 2016 Grammy ceremony. He won three awards – best rap song, best rap performance and best music video – for his smash “HUMBLE.” He also won best rap album for DAMN. and best rap/sung performance for “LOYALTY” (featuring Rihanna).
Lauryn Hill was the first hip-hop artist to win five awards at a Grammy ceremony. She achieved the feat in 1999, though none were in rap categories. She won album of the year and best R&B album for The Miseducation of Lauryn Hill, best rhythm & blues song and best female R&B vocal performance for “Doo Wop (That Thing) and best new artist.
Lamar’s first of three wins for best music video came in 2016 when he won as the featured artist on Taylor Swift’s “Bad Blood.” Swift has won twice in this category. Other artists with two wins are The Beatles, Beyoncé, Johnny Cash, Janet Jackson and Michael Jackson.
Below, take a look at 32 milestones in hip-hop awards history.
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