Robert Earl Keen’s never had a hit—at least not in the traditional chart-topper sense. And he didn’t wear a hat for every album cover, show and publicity shot. He tried but failed to make it in Nashville.

None of that matters. Keen’s songs about the good times and the hard times, and his sardonic wit, amiable stage presence and devotion to the road earned him loyal fans from coast to coast.

Keen’s peers, many of whom are great songwriters themselves, paid him the supreme compliment by p...