As a proud Caribbean woman herself, it only makes sense that Rihanna made one of the best songs on this list. Riding a riddim comes naturally to the Bajan superstar, which is what sets “Work” apart from the rest of the pack. So with her patois on full tilt, an infectious bassline and a melody lifted from Richie Stephens’ Sail Away riddim, Rih brought the pop charts to the dancehall with the Drake-assisted track, spending a few months at the top of the Billboard Hot 100. In fact, it was her longest run at No. 1 ever, proving you can stick to your roots and go pop at the same time.