10 Best Toby Keith Songs

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 rack up accolades for his accomplishments, including induction into the Nashville Songwriters Hall of Fame in 2021, receiving the Merle Haggard Spirit Award from the Academy of Country Music and the National Medal of Arts.

Here are 10 of Toby Keith’s best songs:

10. “My List”
Written by Rand Bishop, Tim James (2002)

What better way to kick off Toby Keith’s best songs than with the aptly named “My List”. While pondering all the chores and tasks he has to do, he pauses to think about what really matters in life and what should be a priority: “Start living, 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 lighthearted tune was polarizing, even for Keith. He said CMT that “Red Solo Cup” was “the dumbest song I’ve ever heard in my life” but also “superb”. 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. “Holidays in Mexico”
Written by Toby Keith (2004)

With “Stays in Mexico”, Keith revisits an old Vegas adage by singing “what happens in Mexico, stays in Mexico”. The song’s main characters, 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 Keith’s first single greatest hits 2 album, reaching No. 3 on the Billboard Chart of hot country songs.

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 image of a man tired of his talkative wife at home, who seeks sanctuary at the local honkytonk. The track was originally recorded by Hank Williams Jr. on his 1992 album maverick. Keith’s version reached #2 on the Billboard Chart of hot country songs.

6. “Beer for My Horses” with Willie Nelson
Written by Scotty Emerick, Toby Keith‎ (2003)

Starring the legendary Willie Nelson, “Beer For My Horses” reflects on the concept of justice amid a tragic news cycle, evoking nostalgia for an era of Western snipers and saloons. The song appears on Keith’s Unleashed album.

5. “As good as I was”
Written by Scotty Emerick, Toby Keith‎ (2005)

In “As Good As I Once Was”, Keith recounts the story of going out with his old pal Dave, who had too many hits and got into trouble at a game of pool, asking Keith for help. He laments that he’s past his early years, but given the chance, “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 of September 11, 2001, several patriotic songs appeared on the country music landscape, including “Courtesy of the Red, White and Blue (The Angry American)”, which was arguably a career-defining moment. by Keith. He vocalized what so many Americans felt after the 9/11 tragedy. A. / Because we’re going to put a boot in your ass / It’s American style. The song was the first single from his album Unleashed and he reached the top of the Billboard Chart of hot country songs.

3. “You shouldn’t kiss me like that”
Written by Toby Keith (2000)

Showing his softer, romantic side, Keith tells the story of friends testing the waters of something more with “You shouldn’t kiss me like that”. The song was the last single from his How do you love me now?! album and it was a #1 hit on the Billboard Chart of hot country songs.

2. “How do you love me now?”
Written by Chuck Cannon, Toby Keith (1999)

In “How Do You Love Me Now?!”, Keith tells the story of a crazed high school musician who is desperate to draw attention to “the perfect and a valedictorian”. He leaves town to follow her dreams and 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 her first major crossover hit, peaking at No. 31 on the Billboard Hot 100.

1. “I should have 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 have done if he had been a cowboy, referencing old Western movies and idealizing the cowboy lifestyle. It was the most played country song of the 1990shelping to define an era of the genre.

Toya J. Bell