Chris Stapleton Covers Willie Nelson’s “Living In The Promiseland” Live on Colbert

Grammy award winner, singer and songwriter Chris Stapleton performed on The Late Show With Stephen Colbert. Stapleton performed “Living in The Promiseland” by Willie Nelson, singer, songwriter and activist. Nelson’s rendition of the song topped the Billboard Country Singles chart 40 years ago upon its release. The song is pro immigration.

Stephen gave a soulful performance, singing with his guitar. He was joined by Nelson’s bandmate, Mickey Raphael, who played harmonica beside Stapleton. At the end of the performance Colbert and Stapleton share a glass of liquor, with Stapleton thanking Colbert and his crew for their kindness on the show. Their four minute performance can be viewed here.

Stapleton will have a busy year as he prepares for his tour across the United States in his All American Road Show from May 23 to October 9. Performing at each destination with several special guests including, Allen Stone, Grace Potter and Maggie Rose. Tickets are on sale now.

Stapleton’s voyage does not stop as he has been announced as one of the line up for the Country Calling Festival on October 2 and October 3, 2026. The festival is in Ocean City Maryland and various country artists will be taking the stage at the festival including, Lainey Wilson, and Rascal Flatts, Dierks Bentley and Miranda Lambert.

Stapleton is a 12 time Grammy award winner. Stapleton earned his first two Grammy wins in his late 30s, including Best Country Album and Best Country Solo performance. With his tributes to Willie Nelson and his packed schedule ahead. Fans can look forward to seeing Stapleton on tour and at the Country Calling Festival.

Photo Credit: Boston Lynn Schulz

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