Duets That Leave Us Guessing Strangest singing duets Rihanna officially crossed over when she performed with a country star at the Academy of Country Music Awards this month.The coupling of a rapper and a country star and animated cat and a former 1980s pop starare two of the oddest singing duos that just can’t be missed. Nelly & Tim McGraw In a split screen video, singing “Over and Over,” Nelly and Tim McGraw proved two chill dudes from two different worlds could be equally lovesick. But honestly, we’re still not sure why. Huey Lewis & Gwyneth Paltrow Before Gwyneth Paltrow graced the "Glee" stage, she performed a duet with a ‘80s pop icon in a movie that’s mostly been forgotten. Words to live by: “Cruisin’ is made for love.” Willie Nelson & Julio Iglesias Imitation is the sincerest form of flattery and often makes for very funny parody. In 1984, Willie Nelson and Julio Iglesias’ duet, “To All The Girls I’ve Loved Before,” got singled out in a comedy show MC Sk