‘Should’ve Been a Cowboy,’ ‘Who’s That Man’ 

Keith’s first single barreled out of the gate with all the speed of Roy Rogers’ Trigger, galloping to Number One on Billboard’s Hot Country Songs chart in just four months. Thirty-one years later, “Should’ve Been a Cowboy” holds up, especially as mainstream country is once again obsessed with cowboy imagery (see Lainey Wilson and Ian Munsick). The lyrics — one of many songs that Keith wrote by himself — evoke the grandeur of the West, but also toss in more than a few references to TV cowboys like Rogers, Gene Autry, and Gunsmoke‘s Matt Dillon. That was Keith recognizing the fantasy of it all: He “should’ve” been a gunslinger, but in real life, he wasn’t. —J.H.

Toby Keith’s cheekiest hit (and one of his very biggest) was this half-rapped “women be talking ” send-up of a man who’s sick and tired of listening to his spouse. Legendary songwriter Bobby Braddock initially pitched the song to a young Blake Shelton, whose team turned it down. But the tale of a guy who’s just not feeling heard resonated with listeners, perching at Number One for five weeks. The song’s genre-hopping was prophetic: “Limp Bizkit’s not out doing Buddy Holly songs,” Keith said at the time. “But they expect our music to sound like Hank Williams and Merle Haggard. We can’t all sound like our past.” —J.A.B.

Consider this Toby Keith’s “Piano Man” — an irresistibly catchy, undeniably crass cinema verité of being a middle-aged bachelor at a small-town bar. Cowritten with his steadfast writing partner Scotty Emerick, “As Good As I Once Was” was another massive 2000s hit for Keith, and probably the only time a song that contemplates erectile dysfunction will ever be named a BMI “Song of the Year.” But Keith’s humor-laced songwriting, his love for common people and all of their high stakes situations in low stakes places, is why this song resonated to the tune of going triple platinum. —S.G.

One of Keith’s most sultry love songs, it carries a hefty dose of caution in its lyrics. “You shouldn’t kiss me like this/Unless you mean it like that,” he sings in the chorus, essentially warning a woman he’s known for a long time that she’s about to leave the friend zone. A track off the 1999 album How Do You Like Me Now?!, it was another Keith solo write that went on to top the charts. Keith prided himself on being a songwriter, even more so than a vocalist: “God forbid, if something ever happened to you and you couldn’t sing no more or perform, you could still write songs,” he said in 2018. But this ballad, exquisitely delivered, proved Keith was one of the genre’s all-time best balladeers. —J.H.

This tall, frosty glass of schadenfreude is quintessential Toby Keith. Lots of singers opine about people who snubbed them in high school, but no one fantasizes aloud quite like Keith: “He never comes home, you’re always alone, and your kids hear you cry down the hall.” The sassy, middle-finger-in-the-rearview anthem reignited Keith’s career, which had been faltering in the late Nineties after a slew of ballads that failed to connect. Keith knew this song would be different. “A lot of people become successful after they’ve been told they won’t ever be,” he said at the time. “It was a fun song to write.” Since fun and vindictive could be close cousins in Keith’s head, execs at the label were reportedly “scared” to put it out. But Keith was more than right. The song became his first crossover hit to land on the Billboard Hot 100 and kickstarted a spree of Number Ones on the country charts in the early 2000s. —S.G.

This duet with country legend Willie Nelson was an undeniably catchy modern-day-cowboy anthem with an anti-crime message that many listeners and critics heard as veering into an open endorsement of vigilante violence. The lyrics decry “too many gangsters doing dirty deeds,“ and offer a grizzly solution: “Take all the rope in Texas, find a tall oak tree/Round up all them bad boys, hang them high in the street,” they sing. Nelson’s fatherly presence on the song certainly helped soften its unforgiving stance. “Beer for My Horses” peaked at Number One on the country chart and stayed there for six weeks. They even adapted it into a movie, starring Keith, Nelson, and the comedian Rodney Carrington. —J.D.

Keith met Clint Eastwood at a celebrity golf tournament and was impressed by the aging Hollywood legend’s zest for life. “I don’t let the old man in,” Eastwood told him. Keith took the phrase and wrote this wrenching acoustic dissertation on mortality: “I wanna live me some more,” he sings over a slow, gentle melody. Keith’s weathered, intimate vocal is especially heartbreaking. When he rides up on his horse/And you feel that cold bitter wind/Look out your window and smile,” he implores. The song was used in Eastwood’s movie The Mule. Keith delivered an extremely moving performance of the song at the 2023 People’s Choice Country Awards. —J.D.

As modern country breakup songs go, it’s hard to beat this one, from Keith’s sophomore Boomtown album. A man and his pickup truck return to their old neighborhood and notice a few changes, like a newly paved road. But then we realize what’s brought him there: His marriage has fallen apart and he’s driving by his old homestead and wondering how his kids are doing. We don’t learn exactly what went wrong and who’s to blame (maybe both parties are?), but as Keith delivers the song in the tone of someone just barely keeping it together, its feeling of regrets and despair are palpable. When Keith sings, “That’s my house and that’s my car/That’s my dog in the backyard,” it’ll hit you no matter whose side of the story you believe. —D.B.

Keith’s uncomfortably titled 2003 LP Shock ‘N Y’all opened with this ode to a watering hole where “walking through the front door puts a big smile on my face.” Keith’s cast of barflies includes ​​yuppies, bikers, and thirsty hitchhikers, girls who dress like movie stars, and veterans who show their battle scars, and he delivers the tune with a warmth that’s made the song a hugely popular happy-hour staple. In 2005, the first I Love This Bar and Grill opened in Keith’s home state of Oklahoma.  —J.D.

Keith wasn’t primarily known for his romantic ballads, but he always made sure to sprinkle them into his albums. And 2002’s Unleashed is no exception — you just had to look a little harder. Buried underneath the thunderous anthem “Courtesy of the Red, White and Blue (The Angry American)” and other hits like “Who’s Your Daddy?” and “Beer for My Horses” is “Huckleberry,” a tender little acoustic ditty about a childhood romance. It’s his very own “Check Yes or No,” featuring a school bus, a county fair, and, eventually, the prom. In classic country song fashion, time passes by (“You’re so extra ordinary sweet like maraschino cherries/We’ll grow up and we’ll get married”) and by its end there’s babies (“Now look at those three little Huckleberries”). The charming track is proof that beyond all the beer-sloshing patriotism, Keith had a soft spot. —A.M.

Written for his friend Wayman Tisdale, Keith initially intended “Cryin’ for Me” (Wayman’s Song) to be the song he’d sing at Tisdale’s funeral after the NBA player and former jazz musician died in 2009. “I wrote this song Sunday morning and tried to prepare myself to sing it,” he said later that year. “I couldn’t get it done, couldn’t get through it. It was too emotional for me.” The resulting tender ballad became a Top Ten country hit for Keith and a touching tribute to a dear friend. “That’s what he was to me,” said Keith, “a gentleman and just the perfect person he was.” —J.A.B.

Just before Gretchen Wilson’s “Redneck Woman,” Keith gave his own ode to women who “ain’t the Barbie Doll type.” For a guy who loved bars this much, nothing activates Keith’s inner-Keats quite like overhearing a lady’s drink order. “She ain’t into wine and roses,” he declares, “and she can’t stand the thought of sippin’ champagne.” This oddly sincere, booze-soaked Valentine gained a permanent slot in Keith’s live shows. The song goes down so smoothly, it’s easy to overlook its quiet moments of honky-tonk poetry, like when he bellows “no Cuervo Gold margaritas” with the gravitas of Richie Havens singing about a motherless child. —S.G.