Album: Damita Jo
Producer: Kanye West
Label: Virgin

Janet already had multiple Billboard hits, world tours, and millions of records sold, while Kanye, fresh off The College Dropout, was just starting a career that seemed destined for greatness. Yeezy quickly gained acclaim as a fashion trendsetter throughout the decade, and with bars like, "This my first Rolex, it don't even be tickin'/This my first pair of earrings I can wear in the shower, without them clouding up in half an hour," this record was Kanye's Swag 101 course.