Upon his 1993 debut single "Should've Been a Cowboy," Toby Keith rode into the country music spotlight as the genre's newest husky-voiced baritone singer and Music Row-ready wordsmith.
From there, he shone as a '90s "hat act" in the same era that brought us Tim McGraw and Kenny Chesney. At the turn of the century, Keith's high-energy material became the focus of a second chapter that also played up his lyrical sense of humor. Being the first name that comes to mind when it comes to 9/11 response songs because of "Courtesy of the Red, White and Blue (The Angry American)" made Keith a household name upon this career shift and still makes the Oklahoma native polarizing.
Heath concerns plus changes in what gets pushed as a country radio hit slowed down Keith's mainstream momentum in recent years, yet he still gets his flowers as one of the most compelling and consistent country stars of his time.
Here's Wide Open Country's 20 favorite Keith songs.
Paul Natkin/Getty Images From the Joe Diffie School of Country Comedy comes this not-so-subtle lust song —as opposed to a love song— filled with truck analogies. It previewed the more comedic elements of Keith's songwriting that's more associated with his 21st century output. Ethan Miller/Getty Images Keith sounds like a particular Country Music Hall of Famer here. This title track from 2008 updates the fiery, rebellious performance style of Jerry Lee Lewis. Kevin Winter/Getty Images. Keith embraced his role as the Lee Greenwood of the new century with this ode to the everyday people that put their lives on the line in the armed forces. It's not Keith's most famous 9/11 response song, but it's his best. Sylvain Gaboury/FilmMagic Keith pokes fun at the toll aging takes on macho bravado with one of his better mid-aughts earworms. Matt Winkelmeyer/Getty Images for iHeartMedia Had someone like Jerry Jeff Walker written about our obnoxious, intoxicated protagonist first, this one might've gotten more benefit of the doubt from those itching to declare country music "dead." In reality, this one's clever in that if you find it a little annoying, it's done its job. KMazur/WireImage One of the best examples of Keith leaning into his pop-rock influences, this Dave Loggins compositions sounds as much like Dire Straits as anything from Keith's formative country radio listening years. Robert Lachman/Los Angeles Times via Getty Images For this boot-scooter, Keith brought to life a character that would've partied hard if he'd existed in the same universe as the Kentucky Headhunter's hell raisers. M. Caulfield/WireImage Great country lyricists dial in on more than the often-indescribable joy of new love and the devastating blow of a breakup. Here and on other songs, Keith masterfully describes the selflessness required for that flame to burn forever. Ron Galella/Ron Galella Collection via Getty Images For Keith's more sensitive side, revisit Blue Moon. A standout along with the pseudo-title track, "Me Too" isn't a wedding song. It's a renewal of vows anthem that celebrates true love while admitting to our limitations at putting those feelings into words. Kevin Winter/ABC/ImageDirect Keith cuts up with the great Willie Nelson on this light-hearted homage to the Wild West mythos. The right balance of silly and sincere makes this among the better Nelson collaborations of its time. Michael Hickey/Getty Images A great vocal performance by Keith, an equally fine effort by some of Nashville's top session players and one of the funnier song concepts from a light-hearted time on country airwaves makes this one an overlooked gem. Rick Diamond/WireImage Keith's first megahit of the new century stands out as more than a textbook example of his tongue-in-cheek style of country comedy (though it was written by veteran songwriter Bobby Braddock and not Keith). This one's all over the place in the best way, with the vocals ranging from rapping to yodeling. Kevin Winter/ACMA2011/Getty Images for ACM It's easy to get caught up in Keith as an ace songwriter or a larger-than-life celebrity and overlook his spot among country music's finest baritone vocalists. His most lovey-dovey hit establishes him as belonging in an elite class as a vocalist. Kevin Winter/Getty Images Instead of longingly looking back at their hometown, our narrator recalls little more than teenage humiliation and heartbreak. It's a nice counter-punch for those of us that never fit in, and reminder that there's nothing sweeter than living above certain others' expectations for us. Tim Mosenfelder/Getty Images Hank Williams Jr. recorded this one first, and Keith stepped up to make it a standard for the country line-dancing crowd. It was an early sign that Keith could make you cry, dance or laugh with any given single. Rusty Russell/Getty Images A Dwight Yoakam-esque taste of Bakersfield, this country-rock stunner deserves the same traditionalist respect as Keith's earliest singles. Ron Galella/Ron Galella Collection via Getty Images The hit that started it all, Keith's debut mainstream single and first No. 1 looked back to the days of Gunsmoke for an ideal of freedom that's guided by a moral compass. It still stands as one of the finest hits from a golden era of country music. Tim Mosenfelder/Getty Images In an interesting twist on breakup songs, Keith's narrator longs for the naive days of new love before he could've seen heartbreak coming from a mile away. It's a benchmark for Keith as a songwriter who's capable of adding nuances to country tradition. Rusty Russell/Getty Images After his image shift from hat act to patriotic pop-country megastar, Keith went back to his roots for one of the best traditionalist country hits of the 21st century. He got help from one of the best, as Dean Dillon co-wrote it with Keith and regular Keith collaborator Scotty Emerick. Paul Natkin/Getty Images Thoroughly fleshed-out characters, from our narrator to his ex and the other man, inhabit a small-town where driving past your old house and seeing someone else's pickup truck in the driveway might as well be inevitable. Though he's excelled in the 30 years since, it remains Keith's greatest contribution to the great American songbook."Big Ol' Truck" (Boomtown, 1994)
"Big Dog Daddy" (Big Dog Daddy, 2008)
American Soldier" (Shock 'N Y'All, 2003)
"As Good As I Once Was" (Honkytonk University, 2005)
"Red Solo Cup" (Clancy's Tavern, 2011)
"Pick 'Em Up and Lay 'Em Down" (Unleashed, 2002)
"Jacky Don Tucker (Play By the Rules)" (Dream Walkin', 1997)
"When Love Fades" (How Do You Like Me Now?!, 1999)
"Me Too" (Blue Moon, 1996)
"Beer For My Horses" (With Willie Nelson) (Unleashed, 2002)
"You Ain't Much Fun" (Boomtown, 1994)
"I Wanna Talk About Me" (Pull My Chain, 2001)
"Does That Blue Moon Ever Shine on You" (Blue Moon, 1996)
"How Do You Like Me Now?!" (How Do You Like Me Now?!, 1999)
"A Little Less Talk and a Lot More Action" (Toby Keith, 1993)
"I'm Just Talkin' About Tonight" (Pull My Chain, 2001)
"Should've Been a Cowboy" (Toby Keith, 1993)
"Wish I Didn't Know Now" (Toby Keith, 1993)
"A Little Too Late" (White Trash With Money, 2006)
"Who's That Man" (Boomtown, 1994)
READ MORE: Toby Keith Through the Years: Look Back at His Life in Photos
Enjoy Country Music?
Sign up for daily stories delivered straight to your inbox.
