Esten played the role of country singer Deacon Claybourne on the drama Nashville from 2012 to 2018, which subsequently kickstarted his own musical career.

Esten was born in Pittsburgh, Pennsylvania and moved to Alexandria, Virginia at age nine, after his parents divorced.

[2] His late father, Charles, was a prominent local businessman and business partner of former Pittsburgh Steelers center Ray Mansfield.

He then attended his parents' and sister's alma mater, the College of William and Mary, where he was a member of Theta Delta Chi fraternity and graduated with a degree in economics in 1987.

Following graduation, Esten moved to the United Kingdom to make his theatrical debut, playing the title role in the musical Buddy in the early 1990s.

[4] Esten's first television appearance was in December 1988 as a contestant on the NBC game show Sale of the Century (under the name Chip Puskar).

He had small roles in three Kevin Costner movies, The Postman, Thirteen Days as downed U-2 pilot Major Rudolf Anderson, and Swing Vote.

[11] On July 25, 2018, Esten was awarded the Guinness World Records title of "The most consecutive weeks to release an original digital single by a music act".

Artists featured throughout the project include Ashley Campbell, Colin Linden, Steve Mandile of Sixwire, Sarah Siskind, Karla Davis, and Miss Jackie Wilson.

On February 4, 2023, Esten filled in as host of the Saturday live performance segment of the Grand Ole Opry, his first appearance in that role.

[17] Esten is national chairman for the annual Light the Night Walks, a fundraiser benefiting The Leukemia & Lymphoma Society (LLS).