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As of 2018, Stapleton has amassed credits writing and co-writing over 170 songs.^[7] He has co-written six number-one country songs^[8] including Kenny Chesney‘s five-week number-one “Never Wanted Nothing More“, Josh Turner‘s “Your Man“, George Strait‘s “Love’s Gonna Make It Alright“, and Luke Bryan‘s “Drink a Beer“.^[9] His songs have appeared on many artists’ albums including Adele, Kelly Clarkson, Brad Paisley, Dierks Bentley, and Taylor Swift.^[10] He has co-written with several artists as well including Vince Gill, Peter Frampton, Sheryl Crow, and Ed Sheeran.^[11]

As a vocalist, Stapleton sang lead in two bands before he started recording as a solo artist including a bluegrass ensemble from 2008 to 2010 called the SteelDrivers and the Jompson Brothers. After that, he released his solo debut: the critically acclaimed studio album titled Traveller (2015), which reached number one on the US Billboard 200 and was certified four-times platinum by the Recording Industry Association of America (RIAA). His version of “Tennessee Whiskey” was certified Diamond by the RIAA. His second studio album From a Room: Volume 1 was released in May 2017, and earned him a second CMA Award for Album of the Year and also a Grammy Award for Best Country Album. From a Room: Volume 2 was released in December 2017. Stapleton released his fourth studio album Starting Over in 2020, for which he won his third Grammy for Best Country Album. The title track was issued as its lead single.

Stapleton has been recognized with several awards including eight Grammy Awards, 10 Academy of Country Music (ACM) Awards, and 14 Country Music Association (CMA) Awards. He was named the ACM’s Artist-Songwriter of the Decade.^[12]