Jesse Winchester was one of the top singer-songwriters of his generation. No less an authority than Bob Dylan was quoted to that effect in the liner notes for Winchester’s Best of CD.
This talented artist was born and raised in the American South, but relocated to Canada to avoid being drafted. His early inability to tour in the US may have permanently stunted his commercial success as a recording artist, since he never achieved sales commensurate with his artistic achievements.
Other performers were quick to recognize the merit of his songs, however, and Winchester has enjoyed consistent success as a songwriter, with other artists recording his compositions. (In this respect, he is similar to, although less prolific than, John Hiatt.)
Winchester’s recognition as a songwriter is well-deserved. He writes compact, intelligent lyrics that betray a wry and piercing self-knowledge. He writes on a variety of themes. His songs about places in the South (“Biloxi”, “Bowling Green”), written while in exile in the cold Northern climes, are as hauntingly evocative as any recorded. “Snow,” from his self-titled debut, and co-written by Robbie Robertson, is a comic look at the plight of an inveterate Southerner stranded in Canada at the start of a long, cold winter. Other songs speak convincingly on philosophical issues, through carefully detailed stories, betraying character through thoughts and actions, and through carefully worded observations of their plights.
Most movingly, though, Winchester writes of the tragic human inability to find lasting love and deep intimacy. In songs like “Yankee Lady,” “The Brand New Tennessee Waltz,” and “Dangerous Fun,” he tells stories about people who find love, and then turn their backs on it, for all too human reasons.
Throughout all of Winchester’s body of work, perhaps influenced by his decision to move to Canada, there is a deep concern for human decisions and their consequences, with a careful eye on what is lost, as well as what is gained, at each fork in the road. His best songs always treat their characters with dignity, and recognition that there are no easy answers to the human dilemma.
Musically, Winchester is today considered a folkie. His earlier work is more in the rock vein, but he seems to have drifted towards folk music simply as an easier, more efficient means of showcasing his songs.
As a singer, Winchester is under-rated. He is always the most intelligent interpreter of his own songs. He has a smooth voice with a broad expressive range, and uses it to great effect on his albums.
Original Release Date: 1989
Rating: 3 Stars (Worthy)
This is an attractively packaged sampler of Winchester’s work, but skips some of his early classics to make room for greater representation from his later albums. The Anthology, listed above, is a better compilation.
Original Release Date: 2000
Rating: 5 Stars (Essential)
This attractively priced two-CD set includes the entire contents of Jesse’s first album, most of the best songs from his second, plus a sampling of tracks from his later releases. Hard to go wrong here.
Original Release Date: 1970
Rating: 5 Stars (Essential)
Winchester’s self-titled debut still seems as fresh, perfect and balanced today as it did when first released. With Robbie Robertson of The Band producing and playing guitar, accompanied by fellow Band-mate Levon Helm on drums and a whole host of excellent Canadian musicians, the accompaniment is first-rate. As a collection of songs, the album is still nearly without peer. Winchester covers all the bases here, with songs about God, sin, good times, casual attraction, and the fragility of love all fitting comfortably together, achieving an effortless thematic cohesion that more pretentious “concept” albums of the day could only strain for. From the dark and brooding “Black Dog” to the comic depiction of a Southerner facing the onset of a Canadian winter in “Snow,” nearly every song is a classic. And while many of these works achieved greater commercial success for the better-known singers who later recorded them, Winchester’s own singing on this album is remarkably strong, versatile and attractive, with unmatched intelligence and understanding gracing every interpretation.
Original Release Date: 1972
Rating: 4 Stars (Recommended)
This was Winchester’s second album. Most of the songs are more sparsely produced than on his first, and the songs are often short and apparently simple — more like sketches in some cases than completed works. But Jesse is in strong voice, the accompaniment is tasteful and supportive, and the songs are almost all gems, featuring beautiful music and interesting, innovative lyrics. A notch below his first album, but still worthwhile.
Next: Quiet About It