CHRIS STAPLETON: May the Fourth Be With You

May 4, 2026

Jimbo,

59th Annual Country Music Association Awards In Nashville — Chris Stapleton performs at the 59th Annual Country Music Association Awards in Nashville, Tennessee, U.S., November 19, 2025. REUTERS/Seth Herald

Chris Stapleton has been able to do some really cool stuff since his career took off. He’s won 11 Grammys, 11 ACMs, 15 CMAs and a whole bunch more. He’s headlined his incredibly successful All-American Road Show since 2017, but he’s also opened for Guns ‘n’ Roses, Tom Petty and the Heartbreakers and The Eagles. He has appeared on Saturday Night Live three times and is a late-night talk show favorite. He was even an extra, a White Walker, on Game of Thrones in 2019.

But there’s one thing that has eluded him and today, May 4th, it haunts him.