Solo studio albums
Stapleton's debut solo album, Traveller, was released on May 5, 2015. It was recorded in Nashville's RCA Studio A. Stapleton co-produced the album with producer Dave Cobb. On the album, Stapleton played guitar and sang with a live band made up of bass player J.T. Cure (from the Jompson Brothers), pedal steel player Robby Turner, drummer Derek Mixon, Mickey Raphael on harmonica, and wife Morgane Stapleton singing harmonies. Stapleton emphasized the importance of the band lineup that came together during the making and promotion of the record. He said his familiarity with Cure and Mixon (he had known and played with Cure for over 20 years), plus Cobb's producing, which included contributing acoustic guitar, had added to the richness of making the record.
Stapleton composed the title track "Traveller" as he and his wife Morgane were driving through New Mexico on their way back to Nashville in a 1979 Jeep that Morgane had bought him, which they had flown to Phoenix, to acquire. She helped Stapleton to sift through 15 years of songs to pick nine to record.
Stapleton won three awards at the 2015 Country Music Association Awards: Album of the Year, Male Vocalist of the Year, and New Artist of the Year. At the CMA Awards, he performed with Justin Timberlake his version of the song popularized as a David Allan Coe live-show staple, "Tennessee Whiskey", and Timberlake's "Drink You Away". This performance was considered a career-defining moment by music publications, and with his wins that night he was lifted to national prominence. In December 2015, Stapleton received the 2015 CMT Artists of the Year Breakout award during a live performance at the annual CMT Artists of the Year show. Traveller was nominated for the Grammy Award for Album of the Year and won the categories Best Country Album and Best Country Solo Performance. It also won the Academy of Country Music Award for Album of the Year and was the top selling country album of 2016. The album had sold a total of 2 million copies in the US by July 2017.
In 2016, Stapleton, with Morgane, contributed the track "You Are My Sunshine" to producer Dave Cobb's compilation record project, Southern Family. Stapleton collaborated with Jake Owen on the song "If He Ain't Gonna Love You" on Owen's album American Love. Stapleton performed on the main stage at the 2016 Country to Country festival in Europe along with Andrew Combs, Kacey Musgraves and headliner Eric Church. Stapleton was the musical guest on the Saturday Night Live episode which aired January 16, 2016, alongside host Adam Driver. Stapleton performed "Parachute" and "Nobody to Blame" from Traveller.
In January 2016, Stapleton performed "Either Way", a song he had written with Kendall Marvel and Tim James, at the Country Radio Hall of Fame's Country Radio Seminar in Nashville. Lee Ann Womack had previously recorded it for her 2008 album, Call Me Crazy. The track was featured on his second studio album, From A Room: Volume 1, released on May 5, 2017. Volume 1 was named after Nashville's RCA Studio A, where it was recorded during the winter of 2016–17. That same month, Stapleton embarked on his All-American Road Show Tour. Volume 1 was certified gold in the US, giving Stapleton his second CMA for Album of the Year, and became the best-selling country album of 2017. Stapleton's third studio album, From A Room: Volume 2, was released on December 1, 2017. Both albums, Volume 1 and Volume 2, debuted at number two on the Billboard 200 charts.
Stapleton was the musical guest on Saturday Night Live for a second time on January 27, 2018, where he performed songs from From A Room: Volume 2 with Sturgill Simpson. In March, "Broken Halos" on From A Room: Volume 1 reached the top of the Country Airplay chart. It earned Stapleton accolades for Song and Single of the Year at the 52nd CMAs. He won Male Vocalist of the Year for a fourth time.
On August 28, 2020, Stapleton released a single, "Starting Over", a song he previously performed on tour. It was the lead single from his album of the same name and was his first single release since 2018's "Millionaire". Stapleton released a second single, "Cold", on September 25. He was Male Vocalist of the Year for the fourth time at the 2021 Country Music Association Awards, and Male Artist of the Year for the third time at the 2022 Academy of Country Music Awards, where he performed "You'll Never Leave Harlan Alive" with Patty Loveless.
