Apparently calling start will create a daemon
thread for playing the clip in the background without blocking until it's ready, and this daemon thread does not cause the JVM to stay alive. Therefore, when your main method ends, so does the clip. Also, when the loop hits the next iteration, the clip is overwritten, causing the existing clip to stop.
If you need to play music files and block until they are done,
you should use either JMF or a third party library. JMF is event based so you'd need to write your own method to wait for the end. A quick approach: