Under the auspices of The Band's Robbie Robertson, Winchester began his recording career in 1970 with his self-titled album, released on the Ampex label.
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Winchester is probably best known as a songwriter, with his works being recorded by many notable artists, including Patti Page, Elvis Costello, Jimmy Buffett, Joan Baez, Anne Murray, Reba McEntire, The Everly Brothers and Emmylou Harris.
Winchester | Winchester College | Winchester, Virginia | Bishop of Winchester | Jesse Ventura | Jesse Owens | Jesse Jackson | Jesse James | Winchester Cathedral | Jesse McCartney | Simon Winchester | Winchester, Massachusetts | Jesse Helms | Diocese of Winchester | Winchester Repeating Arms Company | The Assassination of Jesse James by the Coward Robert Ford | Jesse Spencer | Jesse Johnson | Jesse Ramsden | Jesse Lingard | Jesse Eisenberg | Æthelwold of Winchester | Winchester, Kentucky | Second Battle of Winchester | Jesse May | Jesse Jane | Jesse James (film) | Jesse Ferguson | Jesse Belvin | Conspiracy Theory with Jesse Ventura |
Despite the lack of radio airplay, accomplanying videos for the album's three singles, "High Powered Love", the Cajun-themed "Crescent City", and Jesse Winchester's "Thanks to You", received considerable exposure on CMT.