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Born Donnie Shaquan Lewis, Mad Skillz has long been one of hip-hop’s most respected shape-shifters, and now he’s entering a new era with Grammy recognition to prove it. The Richmond-bred MC, educator, and ghostwriting heavyweight has spent nearly three decades redefining what it means to be an artist, and his latest pivot into spoken word has pushed his legacy even further.

Skillz is widely known as the first rapper to put Richmond, Virginia, on the national hip-hop radar. His 1996 debut From Where??? disrupted the coast-centric rap landscape of the time, proving a kid from VA could rhyme with the best of them. His pen game earned him respect across the industry, leading to collaborations with icons like Missy Elliott and Timbaland, and inspiring the legendary “Rap Up” series: A year-end lyrical recap so influential it became a cultural staple.

But Skillz’s contributions extend beyond music. He’s spent years teaching hip-hop courses at the University of Richmond and was honored with his own city-recognized “Mad Skillz Day” on February 13. His work as an artist, educator, and community voice has cemented him as a cornerstone of Virginia’s creative scene.

Now, Skillz is entering a new chapter. His transition into spoken word poetry has earned him a 2026 Grammy nomination for Words For Days Vol. 1 in the Best Spoken Word Poetry Album category. This comes on the heels of his first-ever artist nomination at the 2025 Grammys for The Seven Number Ones, a deeply personal project unpacking seven pivotal moments from his life. Though he has been nominated before as a writer on Nicki Minaj’s The Pinkprint, these new nods represent his first recognition as a leading artist.

For Skillz, the moment is bigger than trophies: It’s a win for Richmond, for longevity, and for artists daring to evolve. Three decades into his career, he’s proving that vulnerability, versatility, and raw truth can move culture just as powerfully as bars ever did.