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Jim has released five self-produced albums since 2008, when he began performing again after leaving Nashville in 1982.

His first, Reflections, contains twelve of his original songs, arranged in a pleasing country style of music that features keyboards (Anthony Bazzani, Andy Langham and Jim Chesnut), pedal steel guitar (Jerry Blanton and Don Powell), electric lead guitar (Peter Carey and Bobby Flores), acoustic lead guitar (Jerry Blantoni and Bobby Flores), rhythm acoustic guitar (George Chambers and Jim Chesnut),  saxophone and bass Clarinet (John Mill), electric bass (Jim Kalson and Jim Chesnut and drums (Kyle Thompson and Jim Chesnut).

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He released his second album, J.W. Chesnut's Sippin' Whiskey, a roots music anthology, in 2012 with limited indie chart success. He was attempting to gain momentum in the Americana music format, thinking that his style of country music was dead.

But, in December 2013, his single, Get Aboard a Catamaran, one of his originals from the album, reached #12 in the New Music Weekly indie and country charts. His musical identity was beginning to take shape as he began to find his musical brand through the process of elimination.

Assisting Jim on this CD were Jerry Blanton (pedal steel guitar and nylon lead guitar), George Chambers (acoustic rhythm guitar), Hank Harrison (mandoline, electric mandoline and fiddle), Ron Knuth (fiddle), R.J. Smith (fiddle), Michael Waid (slide guitar) and Steve Walden (harmonica).

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Jim released Troubadours and Dreamers, his third self-produced CD in 2014 with the musical assistance of Jerry Blanton and Don Powell (pedal steel guitar) and Alan Kolby (electric lead guitar). Although Chesnut wrote ten of the 12 songs on the album, former Nashville songwriters Steve Collom and Ron Young wrote two of them, Troubadours and Dreamers (Collom) and Right About Now (Young).

It is of special note that one of Jim's songs, Oklahoma Morning, is included in the CD and is a song Charley Pride recorded in the mid-1970s. It was after that that Jim was signed to major publishing and record companies in Nashville.

In 2014, Troubadours and Dreamers was listed as a Top-30 album for the year in the Roots Music Report (RMR) True Country Album Chart, with the single, Oklahoma Morning, reaching #6 in RMR’s True Country Singles Chart and #10 in the New Music Weekly Country Singles Chart.

In 2015, his Another Day in the Life of a Fool debuted at #1 in Roots Music Report’s (RMR) True Country Singles Chart and remained in the top five for several weeks.


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The fourth album, This Guy Sings! (released in early 2016), has really established Jim as an indie country artist to be taken seriously. Since then, Chesnut has had five consecutive national Top-10 indie country singles, including three that made it to #1, according to IndieWorld Country Record Report (IWCRR).

His first self-released single of 2016, Lost and Found Love, became the nation’s #1 indie country record in late May 2016. His second single, True Love Is a Dance in Three Quarter Time, hit #1 in late October 2016.

The third single, A Little More You and a Little Less Me, was released in early November 2016 and reached #1 on March 10, 2017. Circuit Rider peaked at #4 in September in IWCRR and remained #8 in the Euro Academy of Country Music Top-20 chart for several weeks. Chesnut's fifth consecutive national Top-10 single, You Are So Wonderful peaked at #6 in Roots Music Report's Americana Country Top-50 chart in early 2018.

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The fifth CD, I Sure Do Miss My Hair, contains ten Chesnut originals and has just been shipped for distribution (April 10, 2018). It truly represents Jim's tenacity in creating music. After a serious bout with oropharyngeal cancer, chemo and radiation, he has survived and is more determined than ever to leave a quality body of work in his wake.

He was assisted in the production of the album by Jerry Blanton (pedal steel guitar), Alan Kolby (electric lead guitar), and Don McRee (harmonica).