Jesse Winchester’s Country Legacy


jessewinchesterRolling Stone reports that singer-songwriter Jesse Winchester succumbed to bladder cancer Friday morning at the age of 69. He had recently completed work on a new album with Mac McAnally.

Even if you’ve had the misfortune of never encountering any of Winchester’s own recordings, you are very likely already familiar with his work. By the time the tribute album Quiet About It: A Tribute to Jesse Winchester arrived in 2012, the one-time draft dodger’s impressive songbook had already been mined by some of country music’s most discriminating artists (many writers themselves) for more than 40 years. Here, a sampling of some of Winchester’s country cuts dating back to 1971.

“If I Were Free,” Don Williams (2014)

“A Showman’s Life,” Chris Carmack (2013)

“Isn’t That So,” Lyle Lovett (2012)

“Didn’t We Shine,” Randy Travis feat. George Jones, Lorrie Morgan, Ray Price, Connie Smith, Joe Stampley, and Gene Watson (2011)

“A Showman’s Life,” George Strait (2011)

“That’s What Makes You Strong,” Claire Lynch w/ Jesse Winchester (2009)

“Freewheeler,” David Ball (2004)

“A Showman’s Life,” Gary Allan w/ Willie Nelson (2003)

“A Showman’s Life,” Buddy Miller (2002)

“That’s What Makes You Strong,” The Judds (2000)

“Freewheeler,” Michael Martin Murphey (1998)

“Payday,” Elvis Costello (1995)

“Gentleman of Leisure,” Dan Seals (1994)

“O What a Thrill,” The Mavericks (1994)

“Brand New Tennessee Waltz,” Sweethearts of the Rodeo (1993)

“Thanks to You,” Emmylou Harris (1993)

“Just Like New,” Wynonna Judd (1993)

“Didn’t We Shine,” Waylon Jennings (1992)

“Sweet Little Shoe,” Dan Seals (1991)

“You Remember Me,” Reba McEntire (1990)

“Let’s Make a Baby King,” New Grass Revival (1989)

“I’m Gonna Miss You Girl,” Michael Martin Murphey (1988)

“Defying Gravity,” Waylon Jennings (1987)

“Evil Angel,” Ed Bruce (1981)

“How About You,” New Grass Revival (1979)

“My Songbird,” Emmylou Harris (1978)

“Isn’t That So,” Delbert McClinton (1978)

“Biloxi,” Jimmy Buffett (1977)

“Defying Gravity,” Jimmy Buffett (1976)

“Mississippi, You’re on My Mind,” Jerry Jeff Walker (1975)

“Mississippi, You’re on My Mind,” Stoney Edwards (1975)

“Payday,” Flying Burrito Brothers (1973)

“Brand New Tennessee Waltz,” The Everly Brothers (1972)

“Brand New Tennessee Waltz,” Ralph Stanley (1971)


  1. andythedrifter says

    Thanks a lot for this write-up, CM. I’m not yet familiar with Jesse’s own recordings (planning to change that very soon), but I’ve enjoyed a great many songs he has written. Regardless of who sings it, “A Showman’s Life” is one of my favorite songs of all time.

    • says

      “A Showman’s Life” is great. Honestly, I had little idea of how extensively Winchester’s work had been covered in country until putting together this list. Which isn’t even all of it.

  2. says

    “A Showman’s Life” is a great song. And “You Remember Me” is one of my two or three favorite things Reba has ever recorded. Thanks for spotlighting Jesse Winchester’s work. I’m not familiar with many of these songs (yet).


  1. […] I didn’t want to get into this business of trying to be the top shit or something like that. I’d rather just hang in there all the time with good music, slow and steady, and share it, rather than set the world on fire all at once. ‚óŹ – – Singer-songwriter Jesse Winchester, who passed away this week at age 69, to Rolling Stone way back in 1970. Mission accomplished. […]

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