When Hip Hop Meets Country

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  • Snoop Dogg and Willie Nelson
  • Wyclef Jean, Kenny Rogers
  • Coolio, Kenny Rogers
  • Taylor Swift and Nicki Minaj
  • Taylor Swift, Nelly
  • Colt Ford, DMC
  • B.o.B., Taylor Swift
  • LL Cool J, Brad Paisley
  • Nelly, Tim McGraw
  • Jason Aldean, Ludacris
  • T-Pain, Taylor Swift

Coolio, "The Hustler" feat. Kenny Rogers

In 1998, two years before Wyclef's strange mashup, Coolio tapped Kenny Rogers to duet on "The Hustler," a sequal of sorts to "The Gambler."

(Photos from left: Pascal Le Segretain/Getty Images, Slaven Vlasic/Getty Images)