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Stapleton's success was a long time coming. A native of Kentucky -- he was born in Lexington and raised in the smaller Staffordsville -- he moved to Nashville in 2001 in hopes of making it in country music. He signed a publishing deal with Sea Gayle Music and started to work steadily, writing songs and paying bills through various jobs, and playing music all the while. In 2008, he formed the SteelDrivers, a bluegrass group that received quite a bit of acclaim over the next two years. In 2009, the group was named Emerging Artist of the Year by the International Bluegrass Music Association, and the following year they received three Grammy nominations, including Best Bluegrass Album, for Reckless. Despite this success, Stapleton left the group in April 2010 and formed the Jompson Brothers with guitarist Greg McKee, bassist J.T. Cure, and drummer Brad McNamee. By 2013, the Southern rock band was no more, and Stapleton signed with Mercury Nashville, releasing "What Are You Listening To?" in October of that year. The single didn't go anywhere, so its accompanying album was scrapped, and he recorded a new record with co-producer Dave Cobb. This is the album that became Traveller, his solo debut.
Traveller appeared in May 2015 to strong reviews but it didn't do much on country radio; in fact, it was overshadowed by the chart-topping "Crash and Burn," a song Stapleton wrote with Jesse Frasure that was turned into a hit by Thomas Rhett. Nevertheless, its warm reception by critics and peers meant that it racked up a number of CMA nominations and, in a surprise to most observers, it took home three awards that December: Best Male Vocalist, New Artist of the Year, and Album of the Year. Suddenly, Stapleton was a hot property, receiving four Grammy nominations a few weeks after the CMAs, and soon, all that acclaim turned into sales, with Traveller reaching number one on the U.S. country charts and receiving a gold certification from the RIAA, while "Nobody to Blame" became his first country radio hit. "Parachute" charted even higher later in 2016, and Stapleton spent the rest of that year working on his second album with producer Dave Cobb. Recorded at Nashville's RCA Studio A, From A Room was divided into two parts, with the first arriving in May 2017 and the second following later that year. From a Room: Vol. 1 wound up snagging the CMA for Album of the Year prior to the November release of From a Room: Vol. 2. It then won the Grammy for Best Country Album the following spring. Over the next few years, Stapleton remained active in various collaborative projects, co-writing a handful of songs for Justin Timberlake's Man of the Woods album, guesting alongside Bruno Mars on Ed Sheeran's song "Blow," and even appearing as an extra on an episode of HBO's Game of Thrones.
Stapleton returned in 2020 with Starting Over, an album featuring Benmont Tench and Mike Campbell of Tom Petty & the Heartbreakers. Another country chart-topper, it also made a number three showing on the Billboard 200. The following year Stapleton participated in the Metallica tribute project The Metallica Blacklist with a cover of "Nothing Else Matters." ~ Stephen Thomas Erlewine