The 10 Best Chris Stapleton Songs of All-Time

Chris Stapleton

Chris Stapleton is a singer, songwriter, guitarist, and record producer. He moved to Nashville, Tennessee, in 2001 to study for a degree in engineering but then decided to pursue a music career. The same year, Stapleton signed with Sea Gayle Music, who would write and publish his music. Prior to becoming a solo artist, Chris Stapleton was the lead singer of two bands, the Jompson Brothers and the SteelDrivers. He also has credits for writing or co-writing more than 170 songs. Some of the artists who have had hits with songs written by Stapleton include Adele, Dierks Bentley, and Brad Paisley. Stapleton has won ten Country Music Awards, seven Academy of Country Music Awards, and five Grammy Awards. He has released four studio albums, three music videos, one EP, 15 singles, six promotional singles, and eight other charted songs. Here are the 10 best Chris Stapleton songs of all time.

10. You Should Probably Leave (2021)


Stapleton released ‘You Should Probably Leave’ as the second single from his fourth studio album, ‘Starting Over.’ It was written by Stapleton, Chris DuBois, and Ashley Gorley, and Stapleton produced the track with Dave Cobb. Although Stapleton did not release the single until 2021, it was written in 2014, and he had previously performed the song in Nashville with his wife, Morgane. It is about an on-again, off-again relationship.

9. Blow (2019)


Throughout his career, Chris Stapleton has collaborated with other artists. One of his best collaborations was ‘Blow,’ which was a 2019 song recorded with Bruno Mars and Ed Sheeran. It reached number 17 on the Mainstream Rock chart. Although Mars and Sheeran argued during the production of the song, Mars later said it was a privilege to work with both Stapleton and Sheeran.

8. Traveler (2015)


Stereo Gum lists ‘Traveler’ as one of the best Chris Stapleton songs of all time. It was the lead and titular single of Stapleton’s first studio album. It was the first of the artist’s singles to chart on the Billboard Hot 100, and it peaked at number 87. It had greater success on the Hot Country Songs chart, as it reached number 17.

7. Fire Away (2015)


Chris Stapleton and Danny Green co-wrote ‘Fire Away,’ which was a single from Stapleton’s debut album ‘Traveler.’ Stapleton came up with the concept for the accompanying music video, which starred Ben Foster and Margarita Levieva and was directed by Tim Mattia. The song and video are about the different stages of a couple’s relationship and shows landmark events in their life, such as buying a house together. However, the happy times gradually fade away. In 2016, the video won the Music Video of the Year at the Country Music Association Awards.

6. Parachute (2016)


Stapleton co-wrote ‘Parachute’ with Jim Beavers. It is about a man promising to take care of the woman he loves, and the uptempo song is backed by acoustic guitar and banjo. ‘Parachute’ was the third single released from Stapleton’s debut album, ‘Traveler.’ It peaked at number 12 on the Hot Country Songs chart in the United States.

5. Nobody to Blame (2015)


‘Nobody to Blame’ was the second single released from the album ‘Traveler.’ It reached number 10 on the US Country Airplay chart, 11 on the Canada Country chart, and 13 on the Hot Country Songs chart. Stapleton co-wrote this song with Barry Bales and Ronnie Bowman. It is about a man looking back at the end of a relationship.

4. Millionaire (2018)


Chris Stapleton is known for his melancholy tunes, but ‘Millionaire’ is one of his more uplifting singles. The Boot suggests that this is because Stapleton did not write the song, as it was penned by Kevin Welch in 2002. Kevin Welch was also the first artist to release the track, and then another version was released by Solomon Burke in 2006. Stapleton was the third person to release ‘Millionaire’ as a single, and it features Stapleton’s wife, Morgane, singing harmonies in the chorus. The track featured on ‘From a Rom, Vol. 2,’ which was Stapleton’s third studio album.

3. Broken Halos (2017)


‘Broken Halos’ is the only Stapleton single to have topped the US Country Airplay chart. It also reached number three on the country charts in Canada and number five on the US Hot Country Songs chart. The track featured on the album ‘From a Room: Volume 1.’ It was co-written by Stapleton and Mike Henderson, and the lyrics are about people who have passed away before their time.

2. Starting Over (2020)


Stapleton’s second single to top the US Hot Country Songs chart was ‘Starting Over,’ which was the lead and titular single from Stapleton’s fourth studio album. In 2020, Stapleton wiped all his social media profiles clean, then posted a video that showed a preview of ‘Starting Over’ and ‘Watch You Burn.’ ‘Starting Over’ was Stapleton’s first single for two years.

1. Tennessee Whiskey (2015)


‘Tennessee Whiskey’ was a track on Stapleton’s debut album, and it was released as a promotional single in 2015. It was the first of Stapleton’s singles to top the US Hot Country Songs chart. ‘Tennessee Whiskey’ is also the only single of Stapleton’s to become a top 20 hit on the Billboard Hot 100. More than 1.975 million copies were sold, and it was RIAA-certified 7x Platinum. Stapleton was not the first person to release this song, as it was written by Dean Dillon and Linda Hargrove and first recorded by David Allan Coe.

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