“Courtesy of the Red, White and Blue” brought Keith into the consciousness of pop audiences, not so much crossing over as serving as a flash point that illustrated the deepening divisions between blue and red states. The song’s denouement, “We’ll put a boot in your ass/ It’s the American way,” earned the ire of antiwar Americans, including the Dixie Chicks (now known simply as the Chicks), and provoked an intense feud whose scars still linger; after news broke Tuesday of Keith’s death at 62, social media was rife with posts reopening the old wound.

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Keith attempted to walk away from the quarrel not long after it began, telling CMT.com in 2003 “I’m embarrassed about the way I let myself get sucked into all of that,” but “Courtesy of the Red, White and Blue” and its companion hit, “Beer for My Horses” — a rallying call for the revival of lynching, on which he’s accompanied by none other than progressive country hero Willie Nelson, whose appearance plays like an endorsement — cemented the Oklahoma native’s position as one of the key cultural figures of the George W. Bush era: a rabble-rouser writing anthems for sports bars.

The cartoonish caricature, which Keith often happily exploited, obscured the other two acts in his career: his decade of earnest exploration, when he was scoring hits while refining his persona, and the measured, middle-aged music he made after becoming a superstar. “Beer for My Horses” was a callback to the western imagery of his breakthrough single, “Should’ve Been a Cowboy,” but the 1993 hit wasn’t a noxious polemic. Instead, it held a slight air of regret, a realization that life is carrying on without you, a sentiment he also explored on “Who’s That Man,” his next No. 1 hit.

Keith certainly could swagger, happily navigating the honky-tonk shuffle of “You Ain’t Much Fun” and playing with rap cadences on “I Wanna Talk About Me,” inadvertently creating a blueprint for “bro-country” in the process. That broad-chested bravado gave “Courtesy of the Red, White and Blue” and “Beer for My Horses” kinetic energy — a quality distinctly missing from such post-9/11 artifacts as Darryl Worley’s inert “Have You Forgotten?” — but Keith decided not to double down on machismo after he achieved his superstardom.

Success freed Keith to do something that’s still fairly taboo in popular music: accept getting older. Comfortable in his stardom, he started to make subtle gestures: allowing himself to be the punchline of the jokes, deepening his musical roots, embracing the role of an aging outlaw amused by the fact that it takes him a little longer to get up from the floor than it used to. “As Good as I Once Was” in 2005 turned out to be one of his pivotal singles of the mid-2000s, ushering in an era when Keith sang with middle-aged ease, confident in his command as a singer and songwriter. Frequently writing with Scotty Emerick — the pair became frequent collaborators in the early 2000s, scoring their first big hit with “I’m Just Talkin’ About Tonight” — Keith amassed a remarkable catalogue, filling such albums as “Honkytonk University,” “White Trash With Money” and “Big Dog Daddy” with barroom ballads, workingman’s blues and incisive character portraits, punctuating them all with jokes that were too substantial to be called novelties.

The exception to that rule was his last big hit, 2011’s “Red Solo Cup,” a drunken singalong so infectious that it got within spitting distance of the Top 10 on Billboard’s Hot 100. (During the early 2000s, he couldn’t stop releasing drinking songs: The singles “Beers Ago,” “I Like Girls That Drink Beer,” “Hope on the Rocks,” “Drinks After Work” and “Drunk Americans” all followed in quick succession, each receiving slightly less airplay than its predecessor.) And as bro-country became the genre’s dominant strain in the 2010s, Keith relied on a calcifying formula; he ham-fistedly sent up the genre with the single “That’s Country Bro,” delivered in 2019, long after the style’s heyday.

He had one great song left in him, the hushed “Don’t Let the Old Man In,” a bruised ballad that rejected the cowboy mythos he embraced throughout his career. Singing in a whisper supported by a single guitar, Keith produced a final reminder that the connective thread in his music — from the bright rocking country of the ’90s through the overblown patriotism of the W. years and beyond — is providing glimpses of humanity when you least expect them.