Nelly feat. Tim McGraw – Over and Over
In 2004, Nelly was one of the biggest rappers in the world, and Tim McGraw was arguably country music’s biggest star. With the theme of Heartbreak being so universal, it was no surprise the mournful ballad ‘Over and Over’ would be successful with a rap and country collaboration. The unpredictable team-up rocketed the song to No. 3 on the pop chart and tops our list of the best country-rap collaborations of all-time.