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Back to Hip-Hop and R&B Albums: Grammy Wins vs. Losses

1998: Best Rap Album

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Won: 'No Way Out,' Puff Daddy

Should've Won: 'Life After Death,' The Notorious B.I.G.

If you tell a kid these days that Diddy was a rapper, they'd probably laugh in disbelief. Want to know what else is laughable? That Notorious B.I.G.'s sophomore opus 'Life After Death' didn't pick up this Grammy. But in 1998, when he was known to the world as Puff Daddy, Diddy apparently wore his lucky underwear to the 40th Grammy Awards where he scooped the coveted Best Rap Album trophy. He beat out classic albums from Wu-Tang Clan, Missy Elliott, Wyclef Jean and his worthier mentor B.I.G. Like Tupac before him, Biggie had died before being nominated for the award, and ultimately one of rap's biggest pioneers would never receive a Grammy.