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, while the fourth single, 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.

Jim’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.

The 2016 album, This Guy Sings!, was his fourth self-produced CD since 2008.

In 2015, another of his originals, 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.

In 2014, Chesnut’s CD, Troubadours and Dreamers, was listed as a Top-30 album for the year in the RMR’s True Country Album Chart, with the single, Oklahoma Morning, reaching #6 in the True Country Singles Chart and #10 in New Music Weekly’s Country Singles Chart. In December 2013, his single, Get Aboard a Catamaran, reached #12 in New Music Weekly’s indie and country charts.