15 Of Toby Keith's Biggest Country Music Hits

Toby Keith's 20 Biggest Hits

With over 40 million albums sold worldwide, Toby Keith is one of the most popular and influential country music artists of the past 25 years. Since releasing his self-titled debut album in 1993, Keith has become known for his unique blending of traditional country themes and attitudes with a bold, rock-influenced sound.

He has had an astounding number of hit songs that have resonated with country fans, with 20 singles reaching Number One on the Billboard Hot Country Songs chart. Ranging from raucous, beer-drinking anthems to patriotic tributes to tender ballads, the following list showcases some of Toby Keith's biggest chart-topping hits on country radio.

From his breakthrough smash "Should've Been a Cowboy" to more recent number ones like "Made in America," these songs demonstrate Keith's widespread appeal and his major impact on the modern country genre. MC2 Rebekah Blowers, USN/Wikimedia

Should've Been A Cowboy

Toby Keith's 1993 debut single "Should've Been a Cowboy" is an energetic, fast-paced ode to the cowboy lifestyle filled with fiddle and steel guitar. With clever wordplay and a catchy, easy to sing along chorus that proclaims "I should've been a cowboy, I should've learned to rope and ride," the song helped introduce Keith's big personality and rowdy style that would become his signature for decades to come.

Listen to the song on YouTube here. @TobyKeith/YouTube

Beer For My Horses

"Beer for My Horses" finds Toby Keith pairing his gritty, southern drawl with Willie Nelson's wise vocals for a rowdy tale of Western justice. Fueled by driving guitar licks and boozy bravado, the song's vigilante lyrics about hanging bad guys suggest cruising into the sunset with some "beer for my horses" once the righteous work is done. With fun country bravado and an instantly memorable melody, the chart-topper captures Keith's beer-slinging outlaw persona at his peak.

Listen to the song on YouTube here. @TobyKeith/YouTube

He Ain't Worth Missing

"He Ain't Worth Missing" is a quintessential Toby Keith breakup song powered by electric guitar. With its driving percussion and signature country lyricism, the defiant anthem encourages leaving behind a no-good man who doesn't deserve your love. Fueled by Keith's rugged, plainspoken vocals, the track offers a cathartic message to women having man trouble that he just "ain't worth missing."

Listen to the song on YouTube here. @TobyKeith/YouTube

A Little Less Talk and a Lot More Action

"A Little Less Talk and a Lot More Action" packs a raucous punch. Driven by wailing guitars and Keith's classic bravado-filled vocals, the fast-tempo tune demands stopping the chatter in favor of getting down to business between the sheets. With cheeky lyrics centralized around the desire for more intimacy and less talking, it's a rowdy addition to Keith's catalog of songs about man-woman relationships.

Listen to the song on YouTube here. @TobyKeith/YouTube

American Soldier

Toby Keith's "American Soldier" became an enduring patriotic anthem in the post-9/11 era. With earnest lyrics speaking from the perspective of a deployed service member missing loved ones back home, the emotional song pays tribute to the sacrifices soldiers make to defend freedom. Backed by solemn strings and piano, Keith delivers a heartfelt performance that honors the brave men and women in the U.S. armed forces standing strong to protect America's liberty.

Listen to the song on YouTube here. @TobyKeith/YouTube

Wish I Didn't Know Now

"Wish I Didn't Know Now" finds Toby Keith in a somber reflective mood as he sings about the regret and pain that comes with seeing an old love move on. Backed by gentle acoustics and steel guitars, Keith's grizzled yet vulnerable vocals deliver the heartbreaking lyrics wishing he could unlearn harsh truths and go back to happier times of innocence. Though still country to the core, the track reveals Keith's adeptness at more mature emotional storytelling.

Listen to the song on YouTube here. @TobyKeith/YouTube

Red Solo Cup

"Red Solo Cup" became a tongue-in-cheek anthem for Toby Keith fans ready to get the party started. With its singalong chorus praising the iconic plastic party cup as the ultimate vessel for letting loose, the tune captured Keith's skill for quirky storytelling wrapped in a catchy melody. Though silly on the surface, the song displays his mastery of wordplay and relates the nostalgia, camaraderie, and fun times the red cup represents for many.

Listen to the song on YouTube here. @TobyKeith/YouTube

Courtesy of the Red White and Blue

Released in 2002 as a patriotic response to the 9/11 terrorist attacks, “Courtesy of the Red, White and Blue” remains one of Toby Keith’s most recognized and enduring songs. Fueled by his growled vocals and a driving beat, Keith defiantly promises retribution against the nation’s enemies to protect American freedom. With lyrics proclaiming “we’ll put a boot in your ass, it’s the American way”, the bold, uncompromising song connected with a country hungry for justice and still stands tall as a fiery patriotic anthem.

Listen to the song on YouTube here. @TobyKeith/YouTube

Who's That Man

"Who's That Man" immediately catches your attention with dramatic strings and pounding drums, setting the mood for Toby Keith's powerful and commanding performance. With lyrics demanding to know who the mysterious man dancing with his woman is, this song is pure country heartbreak sung with Keith's signature bravado and smooth baritone, augmented by a sweeping string section that amplifies the raw emotion. It showed Keith could deliver the ballad-style emotionality as adeptly as his raucous anthems.

Listen to the song on YouTube here. @TobyKeith/YouTube

As Good As I Once Was

"As Good As I Once Was" shows Toby Keith's comedic songwriting skills in this self-deprecating tale of aging. With his rugged voice backed by steady acoustic guitar, Keith paints a humorous portrait of a formerly wild youth slowed down by injuries and wisdom gained over time. Though he can't party quite as hard anymore, Keith displays his trademark charisma with witty lyrics and a lively, stripped-down sound, proving while he may have lost a step, he's still a top-notch entertainer.

Listen to the song on YouTube here. @TobyKeith/YouTube

I Wanna Talk About Me

"I Wanna Talk About Me" packed Toby Keith's brazen, outspoken personality into one attention-grabbing country rock song. Backed by electric guitar and steady drums, the tune's chorus features Keith unapologetically demanding his share of the conversation focused squarely on himself. With clever lyrics brought to life through his rugged vocals, the song encapsulates Keith's bold, fiery spirit and cemented the bravado-filled themes central to his iconic brand of country music.

Listen to the song on YouTube here. @TobyKeith/YouTube

How Do You Like Me Now?!

"How Do You Like Me Now?!" remains one of Toby Keith's most popular songs, fueled by its fiery chorus and themes of vindication. With driving guitar licks and Keith's defiant vocals, the country rock song calls out an unnamed lover who doubted and rejected him in the past. Now brimming with swagger as a successful musician, Keith boldly takes pride in proving her wrong, cementing his status as an outlaw country star powered by rugged charm and determination through the catchy, cathartic kiss-off anthem.

Listen to the song on YouTube here. @TobyKeith/YouTube

I'm Just Talkin' About Tonight

"I'm Just Talkin' About Tonight" packs all the best elements of his charismatic and rowdy style into one slick country love song. Dripping with bravado over a smooth mix of electric guitar and steady bass, Keith employs his trademark wordplay in pursuit of one goal only - a no strings attached hookup. It's the perfect encapsulation of his ability to blend clever songwriting with his bold, bad boy magnetism.

Listen to the song on YouTube here. @TobyKeith/YouTube

I Love This Bar

"I Love This Bar" became an anthemic ode to Keith's favorite watering hole. With rollicking piano, steady acoustic guitar, and plenty of fiddle, the song paints a lively picture of a beloved local establishment where working folk can kick back with a cold one after a long week. Keith's smooth vocals and inventive lyricism celebrate not just the bar itself, but the community, memories, and pure fun times that happen there every Saturday night.

Listen to the song on YouTube here. @TobyKeith/YouTube

Made in America

“Made In America” finds Keith celebrating the American spirit with heartfelt patriotism. Over swelling strings and gentle acoustics, his smooth baritone lists hard-working American archetypes like farmers, preachers, and resilient small towns. With moving earnestness and uplifting production behind lyrics like “he’s got the red, white and blue flyin’ high on the farm”, the emotional song continues Keith’s tradition of passionate odes that spotlight and honor American pride.

Listen to the song on YouTube here. @TobyKeith/YouTube