Such exuberant joy, such tender innocence, such melancholy longing, such wit and whimsy, such deep philosophical and spiritual wisdom all served up in a two to three minute song with the most delightful and moving melodies and powerful performances.
Whenever we go on a road trip, we make sure to have at least one or two Jesse Winchester cd's in the mix. I once collected his first seven albums into five CD's rearranging his songs into a two-CD collection—"The World According to Jesse"—which contained 46 of his philosophical and spiritual musings; and three single sets: "Mock and Roll" (his humorous songs, his rock songs, and his songs about music), "Pop and Cover" (his own "pop-style" songs and his renditions of other people's songs), and "Love and Loss"
(the contents of which are obvious). I have never done anything quite like this with any other artist. This, I must point out, was before the days of digital playlists and mp3 players.
Jesse Winchester is also my primary example of why a live, solo performance of a truly great songwriter is better than the best recordings. Jesse's albums are pure joy, but his live performances shared an immediacy, intimacy, and intense interpretation that was nearly impossible to capture in the studio.
I love the work of many great songwriters and performers, but if I were doomed to choose only one performer whose catalogue I could listen to, I don't hesitate to say that it would be Jesse Winchester's.
"When I do fall, I will be glad to go," Jesse sang, and I hope that it was true for him. There are many of us who are not glad that he had to go so soon. But as Jesse Winchester sang,
"I wave bye bye
I pray God speed
I wish lovely weather
And all the luck that you need"