19. Sylk-E. Fyne
Major Hit: "Romeo & Juliet" (1998)
Other Hit: "Ya Style" f/ Snoop Dogg & Bizzy Bone (2000)
Did Shakespeare have this in mind? Probably not. But Sylk-E. Fyne had a No. 1 rap hit and Top 10 hit on the Hot 100 in 1998 with "Romeo & Juliet," a thug princess's take on the classic love story. But Sylk-E.'s story didn't end there. She returned to the charts two years later with "Ya Style," featuring Snoop and Too $hort, off her sophomore album, Tha Cum Up.