At his best, Jesse Winchester is an inspired songwriter with a unique worldview. But even at less than his best, he is a craftsman, capable of turning out an album's worth of well-written songs like those here that, now and then, suggest his personal viewpoint. The title track, another of Winchester's reflections on the importance of persevering under difficult circumstances, and "Damned If You Do," which suggests that you might as well follow your heart because you're in trouble either way, are up to his usual standard. But even slight songs like "Everybody Knows But Me" are clever and enjoyable, and overall, Let the Rough Side Drag, with its accomplished mixture of country and R&B, was Winchester's most accessible album so far, even if it was his least ambitious.
AllMusic Review by William Ruhlmann