John Hiatt’s Crossing Muddy Waters was released 25 years ago on September 26th, 2000, during an important turning point in the music industry. If the contents of the album sounded as if they came from a century earlier, its presentation looked to the future.

At the time, Hiatt was a free agent, having recently been set free from Capitol after two studio albums and a best-of package. He and his manager noticed that a group called eMusic1 were leading the race at the time to become the world’s fir...