When the legendary Western swing bandleader Bob Wills showed up to play the Grand Ole Opry in the mid-'40s with a trumpeter and drummer in tow, he was told by Opry officials that “there will be no drums nor horns”—a condition laughable by today’s standards but dead serious back then. Country music has always been a push-pull between tradition and progress, conservatism and cutting-edge. Here’s proof: a playlist full of adventurous contemporary country songs that push boundaries by embracing pop, R&B, hip-hop, rock, and lots more. Our editors regularly update this set with new tracks—if you like something, add it to your library.