What makes the timing so jarring: Anderson had attended the Country Music Hall of Fame's Class of 2026 Medallion Ceremony just that Sunday, October 18.

Tim McGraw, who was inducted into the Hall that same weekend, wrote on social media that he had been talking with Anderson that very night, that Anderson was in such good spirits, and that the two laughed and sang Anderson's songs together. "I am completely heartbroken by his passing," McGraw wrote.

Neither CBS News nor the Associated Press, whose obituary the Chicago Tribune carried, reported a cause of death.

Nashville Public Radio's WPLN frames Anderson's whole character in one story he was proud of: he worked on the roof of the Grand Ole Opry House long before he was ever invited to grace its stage.

WPLN writes that rather than chasing what was popular in the early 1980s, Anderson embraced his thrilling idiosyncrasies as a singer, admired honky-tonk greats like Lefty Frizzell, George Jones and Merle Haggard, and dug gutsily into bluesy bends so his music was instantly recognizable.

Rolling Stone compiled ten essential Anderson performances in tribute, led by "Swingin'", the 1983 CMA Single of the Year that beat efforts by fellow traditionalists Ricky Skaggs, George Jones, and Willie Nelson and Merle Haggard.

Rolling Stone singles out "Seminole Wind" — his self-written 1992 masterclass in setting a sense of place, with a forlorn environmentalist message about the draining of the Florida Everglades — and "Straight Tequila Night," the 1991 No. 1 that revived a career he feared was over.

His catalog also includes "I Wish I Could Have Been There," per the AP.

CBS News reports that years later a mysterious life-threatening illness nearly silenced Anderson, starting with severe headaches in 2016, then hair loss and hearing loss he described as almost complete. "They never really figured out just what it was," Anderson told CBS News in 2022.

WPLN adds that he sought successful treatment at Vanderbilt, then conveyed his gratitude by playing a benefit show at the Ryman Auditorium for the doctors who gave him his music back. He returned with the 2020 album "Years," recorded at Dan Auerbach's Easy Eye Studio.

Rolling Stone notes Anderson said he made it "like it might be the last one I'll do," and that the title track became a late-career standard frequently covered by Sierra Ferrell.

The outpouring shows just how deep Anderson's fingerprints run through modern country. CBS News reports that Blake Shelton collaborated with him, and that Luke Combs and Ashley McBryde recorded his songs for his tribute album, "Something Borrowed, Something New."

The AP writes that Anderson was often identified as a "New Traditionalist" alongside peers like George Strait and Ricky Skaggs, with a gift for bending notes the way George Jones and Merle Haggard did, and that he won CMA album of the year in 1994 for the Eagles tribute "Common Thread," on which he covered "Heartache Tonight."

Yahoo/Tennessean notes his death adds to a difficult year of losses for the country music community in 2026.

Anderson received what he considered the ultimate honor in 2024: induction into the Country Music Hall of Fame, a fact reported by both WPLN and CBS News.

At his induction he reflected: "It's a long, long road from Apopka, Florida, to standing right here on this stage. But I must say … I got to choose my own way. And I said I wouldn't really trade with anyone, because it was my way."

WPLN writes that we can surely hear that in the music he left behind.