From his self-titled debut album in 1993 to his latest release, Peso in my Pocket, in 2021, Toby Keith continues to be a master storyteller. Synonymous with strength, patriotism, and fun, the Oklahoma native has delivered songs for every season of life throughout his nearly 30-year career.
With 32 No. 1 songs and 42 top 10 hits, Keith has created a catalog of music that defines a generation. He continues to accumulate accolades for his achievements, including an induction to the Nashville Songwriters Hall of Fame in 2021, receiving the Academy of Country Music’s Merle Haggard Spirit Award and the National Medal of Arts.
Here are 10 of the best Toby Keith songs:
10. “My List”
Written by Rand Bishop, Tim James (2002)
What better way to kick off the best Toby Keith songs than the aptly named “My List.” While thinking about all the chores and tasks he needs to do, he pauses to think about what really matters in life and what should be a priority: “Start livin’, that’s the next thing on my list.” The song appeared on the Pull My Chain album.
9. “Red Solo Cup”
Written by Brett Beavers, Jim Beavers, Brad Warren, Brett Warren (2011)
Perhaps one of the most recognizable party songs in the country music genre, the light-hearted tune was polarizing, even for Keith. He told CMT that “Red Solo Cup” was “the stupidest song that I have ever heard in my life” but also “freakin’ awesome.” The star-studded music video includes appearances from Jeff Dunham (and his character Bubba J), Carrot Top, Ted Nugent, Sammy Hagar, Craig Ferguson, Geoff Peterson, Roger Clemens, Eric Church, Joe Nichols, Lance Burton, and Larry Bird among others.
8. “Stays in Mexico”
Written by Toby Keith (2004)
With “Stays in Mexico,” Keith puts a twist on an old Vegas adage, singing “what happens down in Mexico, stays in Mexico.” The main characters in the song, Steve from Sioux Falls and Gina from Phoenix, escape their normal lives and have a spontaneous weekend affair south of the border. The song was the lead single off Keith’s Greatest Hits 2 album, reaching No. 3 on the Billboard Hot Country Songs chart.
7. “A Little Less Talk And A Lot More Action”
Written by Keith Hinton, Jimmy Alan Stewart (1993)
Released as Keith’s third single from his self-titled debut album, “A Little Less Talk And A Lot More Action” paints the picture of a man tired of his chatty woman at home, who seeks refuge at the local honkytonk. The track was originally recorded by Hank Williams Jr. on his 1992 album Maverick. Keith’s version reached No. 2 on the Billboard Hot Country Songs chart.
6. “Beer For My Horses” featuring Willie Nelson
Written by Scotty Emerick, Toby Keith (2003)
Featuring the legendary Willie Nelson, “Beer For My Horses” reflects on the concept of justice in the midst of a tragic news cycle, evoking nostalgia for an era of Western gunslingers and saloons. The song appears on Keith’s Unleashed album.
5. “As Good As I Once Was”
Written by Scotty Emerick, Toby Keith (2005)
In “As Good As I Once Was,” Keith tells the story of being out with his old buddy Dave, who had too many shots and got into trouble in a game of pool, asking Keith to help him out. He laments that he’s past his prime years, but if the opportunity arises, “I’m as good once / As I ever was.”
The song appeared on Keith’s Honkytonk University album and won the CMA Music Video of the Year award.
4. “Courtesy of the Red, White and Blue (The Angry American)”
Written by Toby Keith (2002)
After the terrorist attacks on September 11, 2001, several patriotic songs appeared on the landscape of the country music, including “Courtesy of the Red, White and Blue (The Angry American),” which was arguably a defining moment of Keith’s career. He vocalized what so many Americans felt after the tragedy of September 11. “Justice will be served and the battle will rage / This big dog will fight when you rattle his cage / And you’ll be sorry that you messed with / The U.S. of A. / ‘Cause we’ll put a boot in your ass / It’s the American way.” The song was the lead single off his album Unleashed and it reached the top of the Billboard Hot Country Songs chart.
3. “You Shouldn’t Kiss Me Like This”
Written by Toby Keith (2000)
Showing off his softer, romantic side, Keith tells the story of friends who are testing the waters of something more with “You Shouldn’t Kiss Me Like This.” The song was the last single from his How Do you Like Me Now?! album and it was a No.1 hit on the Billboard Hot Country Songs chart.
2. “How Do You Like Me Now?!”
Written by Chuck Cannon, Toby Keith (1999)
In “How Do You Like Me Now?!,” Keith tells the story of a crazy high school musician desperate for the attention “the perfect one and a valedictorian.” He leaves town to follow his dreams and ultimately ends up living in her radio while she picks up the pieces of a broken marriage. The song spent five weeks at No.1 on the Billboard Hot Country Songs chart and It was his first major crossover hit, peaking at No. 31 on the Billboard Hot 100.
1. “Should’ve Been a Cowboy”
Written by Toby Keith (1993)
“Should’ve Been a Cowboy” was Keith’s debut single, setting the tone for his decades-long career. In the song, Keith talks about all the things he could do if he had been a cowboy, referencing old Western movies and romanticizing the cowboy lifestyle. It was the most-played country song of the 1990s, helping define an era of the genre.