Chris Stapleton Takes Political Stand With Willie Nelson Cover

Chris Stapleton isn’t known for making political waves. The Grammy-winning Nashville songwriter typically lets his music do the talking, steering clear of controversy. So when he stepped onto The Late Show With Stephen Colbert’s stage on Wednesday night, his song choice spoke volumes.

Instead of performing one of the countless country hits he’s penned, Stapleton delivered a solo rendition of Living in the Promiseland, the pro-immigrant anthem made famous by Willie Nelson. Written by David Lynn Jones, the song became a Number One country hit for Nelson after appearing on his 1986 album The Promiseland. Backed only by harmonica player Mickey Raphael—the same musician who played on Nelson’s original recording—Stapleton stripped the ballad down to its emotional core. Give us your tired and weak / And we will make them strong, he sang, his guitar and Raphael’s subtle harmonica accents carrying the weight of the song’s message about the American dream.

The timing wasn’t accidental. Nelson, who turned 93 this month, revived Living in the Promiseland last summer during his Outlaw Music Festival Tour, accompanying it with a poignant music video featuring immigrants arriving on America’s shores in search of a better life. Today, that existence feels more elusive than ever, with the current administration actively vilifying immigrants while pursuing aggressive deportation campaigns. Nelson himself emphasized the song’s relevance when he performed it at Constitution Hall in Washington, D.C., while receiving the Gershwin Prize for Popular Song: I think this is one of the most appropriate songs that we could do for this period in America.

For Stapleton to choose this song now—particularly on a major late-night platform—signals a deliberate statement, however quietly made. It’s the kind of move that carries weight precisely because it comes from an artist who rarely steps into the political arena. The choice underscores how country music, rooted in stories of struggle and resilience, still has the power to speak truth when it matters most.

Stapleton is currently on his All-American Road Show Tour and has been nominated for six awards at the upcoming ACM Awards on May 17 in Las Vegas, including Entertainer of the Year. As for Colbert, his show enters its final season, concluding on May 21 after CBS announced cancellation last year—a decision widely speculated to involve pressure from higher corporate levels seeking favor with political interests.