Toby Keith, 1961-2024

David Cantwell's take on the singer's art and legacy

Toby Keith was one of the most popular country singers of the last thirty years: Almost half of his 41 “Top Tens” were #1’s. He was also one of the most influential stars of his era, for both better and for worse. He was a 2015 inductee into the Songwriters Hall of Fame, and, at least among many of the people in my country crowd, was a seriously underappreciated singer. While briskly revisiting his catalog the last couple of days, I was surprised by how his unfussy vocals and storyteller’s phrasing, and his generous tone on hits like “I Love this Bar,” “Getcha Some,” “You Ain’t Much Fun,” and others, put me in mind of a fin de siècle Bobby Bare.

At the same time, Keith was, to put it gently, complicated and difficult, a real “Piece of Work,” as he boasted in a 2004 duet with Jimmy Buffett. Keith cultivated a visceral sense of grievance in nearly all of his best-known numbers. Sometimes those beefs centered, infamously, around politics and the military or, less often and less explicitly, on class-prejudices. Most often, though, they were gender-based and, to his credit and our benefit, those were played at least somewhat for laughs.

“I Want to Talk about Me,” an early country-rap from 2001, was typical on that front. Via flow and chords on loan from The Red Hot Chili Peppers, Keith complained about his chatty girlfriend because she’s always going on about her problems and interests when what he really wanted to discuss was…Toby Keith! Characteristically, his boorishness was playful and clever: “I like talking about you-you-you-you usually / But occasionally…!”

Major hits “Who’s Your Daddy,” “You Ain’t Much Fun” (“It’s honey do this, honey do that!”), and “I’m Just Talkin’ about Tonight,” followed related themes. So did “How Do You Like Me Now?”, where he peevishly berates a woman for passing on him before he was rich and famous. As it played out, “How Do You Like Me Now” was country’s biggest radio hit in 2000. But, because other multi-week chart toppers that year belonged to Faith Hill, Lee Ann Womack, the artists formerly known as Dixie Chicks, and Jo Dee Messina, it was easier to give him the benefit of the doubt. Keith was a petulant loudmouth but good-natured about it and, importantly, was taking part in larger conversations about gender and relationships within the genre. His chart-topping 1993 debut, “Should’ve Been a Cowboy,” became the most-played country-radio single of the Garth-and-Shania decade. Notably, it stood in basic agreement, regarding favored forms of masculinity, with the first new #1 of the following decade, the Chicks’ “Cowboy Take Me Away.”

I quite liked many of Keith’s early hits, but there was no way I could feel generous about Keith’s abhorrent responses to the 9/11 moment. His “Courtesy of the Red, White and Blue (The Angry American),” a full-throated call for gleeful revenge, and the Willie Nelson duet “Beer for My Horses,” about the good old days when lynching parties had after parties, embraced the worst of America. They were embraced by America in return, with both records crossing over into the Pop Top 25. Because the presentation in those numbers of power-as-birthright was so specific, their violences so cold-blooded and presumably so much fun, Keith’s 9/11 songs proved far more chilling and dangerous to me than their closest back-to-back country-hit antecedents, Merle Haggard’s “Okie from Muskogee” and “The Fightin’ Side of Me.” (While I’m on that comparison... Keith’s catalog contained no mitigating humanist masterpieces like “Sing Me Back Home,” “Irma Jackson,” and so on.)

It’s a straight line, I’d say, from “The Fightin’ Side of Me” to Toby Keith’s cruel anthems—and then on to Big & Rich and Montgomery Gentry (who seem to have split between them the joking and earnest halves of Keith’s persona) and from there to contemporary cultural bullies like Jason Aldean. Try that in a small town and we’ll either put a boot up your ass or lynch it.

Keith’s role as an accelerant in that despicable progression will be his legacy—no matter how much some of us may have enjoyed his hit singles, particularly his early, funny ones. I’ll admit I held out hope for a TK redemption arc for a while. He later expressed his regret, if not an apology, for his ugliness while feuding with Natalie Maines and the Chicks. Near the end of Haggard’s life Keith once or twice stepped in at the last minute to lead the Strangers when Merle was too ill to perform. He even played a part, if only on the corporate side, in launching Taylor Swift’s career.

In 2017, though, Toby Keith accepted an invitation to perform at Donald Trump’s inaugural, which was all too viciously on the nose. There’ll be no coming back from that now. –DC

Recommended readings on Toby Keith:

-Alfred Soto, for Humanizing the Vacuum

-Chuck Eddy, for The Village Voice

-Nadine Smith, for Rolling Stone

-Stephen Thomas Erlewine, for The Washington Post

-Bill Friskics-Warren, for The New York Times

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