Most Grammy awards won for Best Country Album by a solo artist

At the 64th Grammy Awards on 3 April 2022, Starting Over by singer/songwriter Chris Stapleton (USA) took Best Country Album. It was his third such award, having won for Traveller in 2016 and From a Room: Volume 1 in 2018. Stapleton cleaned up in three of the Grammys’ four country music categories, scooping trophies for Best Country Song (“Cold”) and Best Country Solo Performance (“You Should Probably Leave”) in addition to Best Country Album. Starting Over, which topped Billboard’s Top Country Albums chart in November 2020, features both tracks.

Best Country Album debuted as Best Country & Western Album in 1965 but was discontinued the following year, with Roger Miller claiming both awards. The category re-surfaced in 1995, and since then has been won four times by the Dixie Chicks (now The Chicks; 1999-2000, 2003 and 2007) and twice by Lady Antebellum (now Lady A; 2011-12), Kasey Musgraves (2014 and 2019) and Miranda Lambert (2015 and 2021). Some of modern country music’s biggest stars – including Reba McEntire, Trisha Yearwood, Brooks & Dunn, Alan Jackson, Garth Brooks, Lee Ann Womack, Tim McGraw, Keith Urban, Brad Paisley, Blake Shelton, Dierks Bentley, Maren Morris and Kenny Chesney – have failed to turn nominations into wins, which makes Stapleton’s success all the more remarkable.

“You Should Probably Leave” was Stapleton’s third win in the Best Country Solo Performance category, after “Traveller” (2016) and “Either Way” (2018). Best Country Solo Performance was inaugurated in 2012 following the amalgamation of the Grammys’ three previous Performance categories. His third award broke a tie with former American Idol winner Carrie Underwood (2013 and 2015). Taylor Swift (2012), Darius Rucker (2014), Maren Morris (2017), Kasey Musgraves (2019), Willie Nelson (2020) and Vince Gill (2021) have been the category’s other winners.

Since 2015, Stapleton has achieved six Top 10 singles on Billboard’s Hot Country Songs chart, including the No.1s “Tennessee Whiskey”, “Starting Over” and “You Should Probably Leave”, which completed its 46-week hike to No.1 on 19 February 2022.