Toby Keith, a towering figure in country music known for his charismatic persona and powerful baritone, left an indelible mark on the genre with songs that resonated deeply with audiences. From humorous anthems to heartfelt ballads and patriotic tributes, his music traversed a range of emotions and experiences, solidifying his place as one of the most influential artists of his generation. Following his passing at 62 after a courageous battle with stomach cancer, it’s fitting to revisit some of the best Toby Keith Songs that defined his career and cemented his legacy.
‘Should’ve Been a Cowboy’ (1993)
Toby Keith performs at Shoreline Amphitheatre on October 14, 1993 in Mountain View California.
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“Should’ve Been a Cowboy,” Toby Keith’s debut single, burst onto the scene with the energy of a runaway train, rapidly climbing to the top of Billboard’s Hot Country Songs chart. Even three decades later, this track remains a quintessential country anthem, especially relevant in today’s country landscape that once again embraces cowboy themes. Penned solely by Keith, the lyrics paint a vivid picture of the romanticized West, peppered with nods to iconic TV cowboys like Roy Rogers, Gene Autry, and Gunsmoke‘s Matt Dillon. This song acknowledged the allure of fantasy, with Keith playfully admitting he “should’ve” been a gunslinger, while grounded in the reality of modern life. It’s a testament to the enduring appeal of cowboy imagery and one of the defining Toby Keith songs.
‘I Wanna Talk About Me’ (2001)
Toby Keith during Country Recording Artist Toby Keith Performs at One51 in New York City, New York, United States.
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One of Toby Keith’s most playful and commercially successful hits, “I Wanna Talk About Me,” is a tongue-in-cheek commentary on relationships, delivered with a rap-influenced rhythm that was groundbreaking for country music at the time. Initially offered to Blake Shelton, the song found its perfect voice in Keith, whose rendition of a man craving a moment to be heard struck a chord with listeners. It dominated the Number One spot for five weeks, proving Keith’s finger was firmly on the pulse of what resonated with audiences. Keith himself recognized the song’s genre-bending nature, stating that country music shouldn’t be confined to its past sounds. This hit showcased his willingness to experiment and push boundaries, making it a standout among Toby Keith songs.
‘As Good As I Once Was’ (2005)
Toby Keith performs in support of his
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Often likened to Toby Keith’s version of “Piano Man,” “As Good As I Once Was” is an incredibly catchy and humorously honest portrayal of middle-aged life in a small-town bar. Co-written with his long-time collaborator Scotty Emerick, this song became another massive hit in the 2000s for Keith. Its relatable lyrics, which even touch upon themes of aging and physical changes with a lighthearted approach, resonated deeply with fans. The song’s ability to find humor in everyday situations and connect with ordinary people is a hallmark of Keith’s songwriting. The fact that a song contemplating such themes could achieve BMI “Song of the Year” status speaks volumes about its impact and popularity, solidifying its place among the best Toby Keith songs.
‘You Shouldn’t Kiss Me Like This’ (2000)
Toby Keith performs his set at the KIKK/KILT Country Jam Saturday, Oct. 28, 2000, in The Woodlands, Texas.
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“You Shouldn’t Kiss Me Like This” showcases Toby Keith’s ability to deliver a sultry love song with a touch of caution. This track carries a lyrical warning, with Keith singing about the potential consequences of a passionate kiss between long-time friends. Featured on his 1999 album How Do You Like Me Now?!, this self-penned ballad topped the charts, highlighting Keith’s prowess as a songwriter and vocalist. He considered songwriting his primary strength, believing it would endure even if his performing career ended. This ballad, with its exquisite delivery and emotional depth, proved Toby Keith was also among the genre’s finest balladeers, adding another dimension to his repertoire of Toby Keith songs.
‘How Do You Like Me Now?!’ (1999)
Toby Keith during 34th Annual Academy of Country Music Awards at Universal Ampitheater in Universal City, California, United States.
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“How Do You Like Me Now?!” is pure, unadulterated Toby Keith, a potent cocktail of schadenfreude and swagger. While many artists sing about high school rejection, few do it with Keith’s level of unapologetic bravado. This anthem of vindication reignited Keith’s career after a period of less successful ballads in the late Nineties. He recognized the song’s unique appeal, understanding its resonance with those who had overcome doubt and adversity. Despite label concerns about its sassy and slightly vengeful tone, “How Do You Like Me Now?!” became Keith’s first crossover hit on the Billboard Hot 100, launching a string of Number One country hits in the early 2000s and firmly establishing it as one of the most recognizable Toby Keith songs.
‘Beer for My Horses’ (2003)
Toby Keith and Willie Nelson during "Willie Nelson and Friends: Live and Kickin
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A duet with country music legend Willie Nelson, “Beer for My Horses” is an undeniably catchy, modern-day cowboy anthem with a strong stance against crime. While some critics interpreted its anti-crime message as advocating vigilante justice, the song’s popularity was undeniable. The lyrics, lamenting the prevalence of “gangsters doing dirty deeds” and suggesting a harsh solution, sparked debate but also resonated with a segment of listeners. Willie Nelson’s iconic presence softened the song’s potentially harsh edges for some. “Beer for My Horses” topped the country chart for six weeks and even inspired a movie starring Keith and Nelson, further cementing its place in popular culture and as one of the most discussed Toby Keith songs.
‘Don’t Let the Old Man In’ (2018)
Toby Keith performs during Country Thunder Music Festival Arizona – Day 3 on April 7, 2018 in Florence, Arizona.
Image Credit: Rick Diamond/Getty Images for Country Thunder USA
“Don’t Let the Old Man In” offers a different side of Toby Keith, a reflective and poignant meditation on mortality inspired by a conversation with Clint Eastwood. Impressed by Eastwood’s vitality at an older age, Keith took Eastwood’s phrase “I don’t let the old man in” and crafted this moving acoustic ballad. The lyrics express a desire to embrace life fully, even as time passes. Keith’s weathered and intimate vocal delivery adds to the song’s emotional weight. Featured in Eastwood’s movie The Mule, the song gained further recognition and resonated deeply with audiences. Keith’s performance of this song at the 2023 People’s Choice Country Awards was particularly moving, showcasing the song’s power and emotional depth, marking it as a standout among later Toby Keith songs.
‘Who’s That Man’ (1994)
Toby Keith at the Holiday Star Theater in Merrillville, Indiana, January 25, 1994.
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As far as modern country breakup songs go, “Who’s That Man” from Toby Keith’s Boomtown album is a hard one to surpass. The song depicts a man returning to his old neighborhood after a separation, noticing subtle changes that amplify his sense of loss. The listener gradually understands the depth of his pain as he drives past his former home, contemplating his children’s well-being. The song masterfully conveys regret and despair without explicitly assigning blame, allowing listeners to connect with the raw emotion of heartbreak. When Keith sings about his house, car, and dog now belonging to a changed reality, it evokes a powerful sense of longing and loss, making it a deeply resonant Toby Keith song.
‘I Love This Bar’ (2003)
Toby Keith during Toby Keith in Concert in Los Angeles on August 25, 2003 at Staples Center in Los Angeles, California, United States.
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Toby Keith’s album Shock ‘N Y’all opened with “I Love This Bar,” an anthem celebrating the simple pleasures of a local watering hole. The song paints a vivid picture of a diverse bar crowd, from different walks of life finding common ground in this unpretentious space. Keith’s warm delivery and relatable lyrics have made this song a popular choice for happy hour gatherings and a testament to the communal spirit of bar culture. Its popularity extended beyond music, with the opening of the first I Love This Bar and Grill in Oklahoma in 2005, further solidifying the song’s cultural impact and recognition as one of the most beloved Toby Keith songs.
‘Huckleberry’ (2002)
Country artist Toby Keith performs at the Thomas & Mack Center November 1, 2002 in Las Vegas, Nevada. Keith is touring in support of the new album,
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While Toby Keith was renowned for his up-tempo anthems, he consistently included romantic ballads in his albums. “Huckleberry,” from 2002’s Unleashed, is a tender acoustic song about childhood sweetheart romance. Often overshadowed by the more bombastic hits on the album, “Huckleberry” reveals a softer side of Keith’s artistry. It’s a nostalgic journey through young love, reminiscent of classic country storytelling, depicting innocent moments like school bus rides, county fairs, and prom nights. The song beautifully portrays the progression of time and love, culminating in family life. This charming track demonstrates that beyond the patriotic persona, Toby Keith possessed a tender heart, making “Huckleberry” a hidden gem among Toby Keith songs.
‘Cryin’ for Me (Wayman’s Song)’ (2009)
Toby Keith performs during the Nobel Peace Prize Concert at Oslo Spektrum on December 11, 2009 in Oslo, Norway.
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“Cryin’ for Me (Wayman’s Song)” is a deeply personal and emotional ballad written by Toby Keith as a tribute to his friend Wayman Tisdale, the NBA player and jazz musician who passed away in 2009. Initially intended for Tisdale’s funeral, the song proved too emotionally overwhelming for Keith to perform at the service. This tender ballad became a Top Ten country hit and a poignant expression of grief and friendship. Keith’s heartfelt delivery and the song’s raw emotion resonated with listeners, turning personal sorrow into a universally relatable tribute. “Cryin’ for Me (Wayman’s Song)” stands as a testament to the depth of Keith’s emotions and his ability to translate them into powerful music, making it a deeply moving Toby Keith song.
‘Whiskey Girl’ (2003)
Live performance of country western singer Toby Keith at the Staples Center.
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Preceding Gretchen Wilson’s “Redneck Woman,” Toby Keith offered his own ode to women who defy conventional stereotypes with “Whiskey Girl.” For an artist who celebrated bar culture, Keith found inspiration in a woman’s drink order, appreciating those who preferred whiskey to more delicate beverages. This song is a sincere, if slightly boozy, Valentine to women who are authentic and unpretentious. It became a staple in Keith’s live performances, showcasing his ability to blend humor and genuine appreciation in his music. Despite its lightheartedness, “Whiskey Girl” features moments of honky-tonk poetry, revealing Keith’s knack for finding beauty in unexpected places and solidifying its place as a fan-favorite Toby Keith song.
Toby Keith’s vast catalog is filled with songs that have touched hearts, sparked laughter, and stirred emotions. These selected tracks represent just a glimpse into the breadth and depth of his artistry, showcasing his talent as a songwriter, vocalist, and entertainer. His music continues to resonate with fans, ensuring his enduring legacy as a country music icon through his timeless Toby Keith songs.
