We may have known about Toby Keith's stomach cancer diagnosis for nearly two years, but that didn't keep the news of his Feb. 5 death from hitting hard. The oftentimes outspoken country music star enjoyed a three-decade career as one of the genre's beloved hitmakers, courtesy of unabashed hits like "Who's Your Daddy?," "Made In America" and "I Wanna Talk About Me."
Occasionally his in-your-face persona clashed with folks, particularly when it came to his political views in recent years. But for the most part, it was Keith's blue-collar upbringing and work ethic that shined through and resonated with his legion of listeners.
It wasn't until his thirties that the future Songwriters Hall of Famer landed his first record deal in 1993, following years grinding away as a rodeo hand, in oil fields and as a semi-professional football player to make ends meet. The Oklahoma-born crooner would go on to record 20 No.1 hits, sell over 40 million records across 26 albums, and gross nearly $400 million touring — cementing himself as one of country music's most successful artists in the process.
As we look back on Keith's life and legacy, here are five essential cuts from the seven-time GRAMMY nominee, whose memory will live on in the hearts of country music artists and fans alike.
"Should've Been A Cowboy" (1993)
Few artists strike gold with their maiden release, but Keith did just that when his song "Should've Been A Cowboy" launched in February 1993. The upbeat track received widespread acclaim, eventually reaching No. 1 on the Billboard's Hot Country Songs chart a few months later.
"Should've Been A Cowboy" takes on a distinctly traditional tone as Keith romanticizes cowboy culture by referencing classic westerns like Gunsmoke with nods to Marshall Dillon and Miss Kitty in addition to six-shooters, cattle drives and Texas Rangers abound. The tune also reinforces the notion that cowboys just have more fun, whether its "stealin' the young girls' hearts, just like Gene [Autry] and Roy [Rogers]" or "runnin' wild through the hills chasin' Jesse James."
By the looks of Keith's career, he certainly had his fair share of fun, and it may not have come if it weren't for "Should've Been A Cowboy."
"How Do You Like Me Now?!" (1999)
After a successful '90s run (which included two more No. 1s in "Who's That Man" and "Me Too"), Keith kicked off the 2000s with his fourth No. 1 hit, "How Do You Like Me Now?!" In signature Toby Keith fashion, he confronts his haters by asking the titular, rhetorical question, posed to his high school's valedictorian — who was also his crush. "I couldn't make you love me but I always dreamed about livin' in your radio," he sings on the brazen chorus.
The song is a stern reminder to never let anyone keep you from chasing your dreams; it's also a lesson of standing strong on your convictions. Its message also proved fitting for Keith's career: After Mercury Records Nashville rejected the song (and its namesake album) in the late '90s, Keith got out of his deal with them in favor of signing with DreamWorks Records, with whom he released the project a year later. Not only did the single go on to spend five weeks at No. 1 on the Hot Country Songs chart, but it became the singer's first major crossover hit.
"Courtesy of the Red, White and Blue (The Angry American)" (2002)
Keith was never afraid to share his opinion in public or in song, especially when it came to displaying his patriotism and appreciation for those who protect the United States. While the Okie approached this from a softer side on 2003's "American Soldier," his most renowned musings on the subject without a doubt came a year earlier with "Courtesy of the Red, White and Blue (The Angry American)."
On the angsty ballad — which was written in the wake of his father's March 2001 death and the Sept. 11, 2001 terrorist attacks — Keith channels a universal feeling of American hurt and pride. "Courtesy of the Red, White and Blue (The Angry American)" inspired an equal outpouring of support and outrage that, for better or worse depending on where you stand, helped cement the song into the annals of country music lore.
"I Love This Bar" (2003)
We've all got our favorite watering hole full of its own quirks and characters, from winners to losers, chain-smokers and boozers. Keith taps into that feel-good, hometown hang feeling with "I Love This Bar," a lighthearted tale from 2003's Shock'n Y'all that makes dingy dive bars feel like the prime party destination.
The midtempo track — Keith's 12th No. 1 — further plays into country music drinking tropes as Keith proclaims, "I like my girlfriend, I like to take her out to dinner, I like a movie now and then" before making a hard pivot, adding "but I love this bar."
All joking aside, the song, and all of the unique individuals described within it, have a harmony to them inside those hallowed walls. It's a kinship that seems more and more difficult to find in today's world, and a sentiment best captured at the song's conclusion: "come as you are."
"As Good As I Once Was" (2005)
Your best days may be behind you, but that doesn't mean you can't still live your best life and thrive in the present — even if you don't get over hangovers as quickly as you used to.
That youthful wisdom is distilled into every lyric of "As Good As I Once Was," a reminiscent story in which a then-44-year-old Keith recounts his prime as a lover, drinker and fighter humbly. That being said, his pride is still quick to take charge with convictions like "I still throw a few back, talk a little smack, when I'm feelin' bullet proof."
Lasting six weeks at No. 1, "As Good As I Once Was" was the biggest of the 15 chart-toppers Keith tallied in the 2000s. And though he scored one more in the following decade (along with several other hits, including the playful drinking song "Red Solo Cup"), "As Good As I Once Was" will live on as one of Keith's quintessential messages of fun-loving confidence: "I ain't as good as I once was, but I'm as good once, as I ever was."
8 Artists Bringing Traditional Country Music Back: Zach Top, Randall King, Emily Nenni & More On Why "What's Old Becomes Beloved Again"