Chris Stapleton’s Flawless Take on Willie Nelson’s Classic Leaves Fans in Awe

​Chris Stapleton, renowned for his soulful blend of country, blues, and rock, has consistently honored the legends who paved the way before him. His deep admiration for Willie Nelson, a cornerstone of country music, has been evident throughout his career. This reverence culminated in a heartfelt tribute during the “Austin City Limits Celebrates 50 Years” special, where Stapleton delivered a stirring rendition of Nelson’s classic “Angel Flying Too Close to the Ground.”​

“Angel Flying Too Close to the Ground” holds a special place in Willie Nelson’s repertoire. Originally written for the 1980 film Honeysuckle Rose, the song’s poignant lyrics and emotive melody have resonated with listeners for decades. Nelson’s ability to craft songs with universal themes is exemplified in this track, which he describes as intentionally open to interpretation, allowing listeners to find personal meaning within its verses. ​

Stapleton’s connection to Nelson’s music runs deep. Before achieving solo stardom, Stapleton was a prolific songwriter, penning hits for artists like Kenny Chesney and George Strait. His appreciation for Nelson’s artistry became publicly evident during a 2017 performance at George Strait’s Hurricane Harvey relief concert, where Stapleton delivered a soul-stirring cover of “Angel Flying Too Close to the Ground.” This rendition showcased his ability to channel raw emotion, echoing the heartfelt sincerity that Nelson is known for. ​

In September 2024, Stapleton appeared on The Howard Stern Show, where he once again paid homage to Nelson by performing “Angel Flying Too Close to the Ground.” This performance was met with widespread acclaim, with fans praising Stapleton’s effortless delivery and blues-infused interpretation. The rendition garnered significant attention online, amassing over 130,000 views and reinforcing Stapleton’s reputation as one of the most talented artists of his generation. ​

The culmination of Stapleton’s tributes to Nelson was his participation in the “Austin City Limits Celebrates 50 Years” special, which aired on PBS on April 4, 2025. This milestone event featured performances from a diverse array of artists, including Lyle Lovett, Billy Strings, and Brandy Clark, all honoring the rich history of the iconic music series. Stapleton’s choice to perform “Angel Flying Too Close to the Ground” was particularly poignant, as Nelson had appeared on the pilot episode of Austin City Limits in 1974, helping to launch what would become the longest-running music series in television history. ​

Stapleton’s rendition during the special was a masterclass in musical homage. His rich, textured vocals breathed new life into the classic, while his nuanced guitar work paid subtle tribute to Nelson’s distinctive style. The performance served not only as a celebration of Nelson’s enduring legacy but also as a testament to Stapleton’s deep respect for the traditions of country music.​

Beyond these performances, the bond between Stapleton and Nelson has been evident in various collaborations. In 2023, Stapleton joined Nelson on stage during Nelson’s induction into the Rock & Roll Hall of Fame, further solidifying their mutual admiration. Additionally, Nelson recorded “Our Song,” a ballad penned by Stapleton, for his own album, highlighting the trust and respect between the two artists. ​

Stapleton’s tributes to Nelson, particularly his renditions of “Angel Flying Too Close to the Ground,” underscore the cyclical nature of musical inspiration. Just as Nelson’s work has profoundly influenced Stapleton, so too does Stapleton’s interpretation introduce Nelson’s classics to new audiences, ensuring their timeless resonance. Through these performances, Stapleton not only honors the past but also bridges it to the present, embodying the enduring spirit of country music.

If you want more music and videos from Chris Stapleton, check out his YouTube Channel. Fans can also connect with him on Instagram and Facebook. Get news, updates, and tour info on his official website.