In a little over a month Winchester found himself playing guitar in the band Les Astronauts before going solo as a regular at coffeehouses around Montreal. During one such foray in Toronto, he was spotted by Robbie Robertson of The Band and was enticed into recording an album that Robertson would produce. His self-titled debut on Ampex Records featured guest performances by David Rea, Al Cherney, Ken Pearson, Bob Boucher, David Lewis, Gary Black, and fellow The Band member Garth Hudson. With inconsistent gaps between albums, Winchester found fame behind the scenes writing material that was being made into hits for others - The Everley Brothers, The Weather Girls, Jimmy Buffett, Joan Baez, and The New Grass Revival to name but a few. But A Breeze' when the U.S. government gave draft dodgers amnesty.
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