#Rapper · IMissIt.com

Celebrities 1996–2002 peak

Busta Rhymes

The human cartoon of 90s rap—hip-hop's most watchable man, a blur of dreadlocks and rubbery limbs who moved like he was made of springs. Trevor Smith stole posse cuts for a living and built a solo career on being impossible to look away from.

Video thumbnail — DMX - Party Up (Up In Here) (Enhanced Video, Edited)

Celebrities 1998–2003 peak

DMX

The barking Yonkers growl who crash-landed on the glossy late-90s rap charts like a dog off its chain. Earl Simmons snarled prayers over Swizz Beatz beats, made Ruff Ryders a household name, and opened a #1 movie at the box office. Equal parts menace and open wound, he was hip-hop's most ferocious voice when it needed one most.

Video thumbnail — JAŸ-Z - Izzo (H.O.V.A.)

Celebrities 1998–2009 peak

Jay-Z

Shawn Corey Carter rose from Marcy Projects hustler to rap's defining CEO, making the 2000s the decade when hip-hop conquered the boardroom. His Imperial period—from Hard Knock Life through The Black Album and beyond—turned street rap into stadium singalongs and Grammy gold. Jay-Z didn't just make hits; he made an industry, proving rappers could own their own records and empires. The 2000s belonged to him.

Celebrities 1994–1997 peak

The Notorious B.I.G.

Brooklyn's rap king — Christopher Wallace, aka Biggie Smalls — whose effortless flow and vivid street storytelling made him the defining East Coast voice of the mid-90s. His 1997 murder, still unsolved, cut short one of hip-hop's greatest careers at just 24.