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 sixth and final single from This Guy Sings!, his fourth self-produced CD since 2008, was Unfinished Business. It was released just after Jim completed chemo and radiation treatment for oropharyngeal cancer in the fall of 2017 and reached IndieWorld Country Record Report's Top-10 in mid-June of 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.