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Toby Keith's Top 20 Songs, Ranked

Get ready to tip your cowboy hat and crank up the volume because we're about to take a honky-tonk journey through the heart and soul of America with none other than Toby Keith himself.

From the dust-kicked roads of Oklahoma to the neon lights of Nashville, Toby Keith has become synonymous with the kind of country music that grabs you by the soul and refuses to let go. We're not counting down just any list. We're striding through the saloon doors of musical greatness to bring you Toby Keith's 20 best songs, ranked.

Whether you're a longtime fan or just getting acquainted with the powerhouse behind hits like "Should've Been a Cowboy" and "Red Solo Cup," prepare for a ride through tales of love, liberty, and the pursuit of cold beer. Grab a cold one, and let's pay homage to the tracks that have made Toby Keith (who died in 2024) a legend in the world of country music.

"Who's That Man"

"Who's That Man"
  • Released: 1994
  • Peak US Hot Country Songs (Billboard) Chart Position: #1
  • Weeks on Chart: 20

"Who's That Man"  is a poignant country ballad that explores the themes of regret, redemption, and second chances. With its emotive lyrics and soulful melody, the song tells the story of a man reflecting on the consequences of his actions and seeking forgiveness for his past mistakes. Especially when he drives by his former house and sees someone else with his ex. That man is literally living the life Toby could have been living.

(Image via PolyGram/Polydor Nashville 853358)

"Love Me If You Can"

"Love Me If You Can"
  • Released: 2007
  • Peak US Hot Country Songs (Billboard) Chart Position: #1
  • Peak US Billboard Hot 100 Chart Position: #48
  • Weeks on Chart: 20

"Love Me If You Can" is a thought-provoking country song that challenges listeners to examine their beliefs and values about love, justice, and humanity. With its powerful lyrics and compelling melody, the song encourages empathy and understanding in a world filled with complexities and contradictions.

(Michael Tran/FilmMagic/Getty Images)

"Getcha Some"

"Getcha Some"
  • Released: 1998
  • Peak US Hot Country Songs (Billboard) Chart Position: #18
  • Weeks on Chart: 20

"Getcha Some" is an energetic country song that humorously portrays the pursuit of romantic interests and the thrill of dating. With its catchy melody and playful lyrics, the song captures the excitement and confidence of the protagonist as he advises others to seize the opportunity for love and adventure.

(JO1 Benjamin Franklin, Public domain, via Wikimedia Commons)

"She Never Cried in Front of Me"

"She Never Cried in Front of Me"
  • Released: 2008
  • Peak US Hot Country Songs (Billboard) Chart Position: #1
  • Peak US Billboard Hot 100 Chart Position: #42
  • Weeks on Chart: 20

"She Never Cried in Front of Me" is a poignant country ballad that explores the pain of heartbreak and the facade of strength maintained in tough times. With its emotional lyrics and heartfelt delivery, the song resonates with listeners, capturing the raw vulnerability of love lost. 

(Sgt. Joshua LaPere, Public domain, via Wikimedia Commons)

"My List"

"My List"
  • Released: 2001
  • Peak US Hot Country Songs (Billboard) Chart Position: #1
  • Peak US Billboard Hot 100 Chart Position: #26
  • Weeks on Chart: 31

"My List" is a heartfelt country ballad that emphasizes the importance of love and relationships over material possessions. With its touching lyrics and emotional delivery, the song resonates with listeners, reminding them of the significance of the little things that make life meaningful.

krasyuk - stock.adobe.com

"Whiskey Girl"

"Whiskey Girl"
  • Released: 2004
  • Peak US Hot Country Songs (Billboard) Chart Position: #1
  • Peak US Billboard Hot 100 Chart Position: #31
  • Weeks on Chart: 20

"Whiskey Girl" is a lively country-rock anthem that celebrates the joys of good company and whiskey. With its upbeat rhythm and catchy chorus, the song became a fan favorite, showcasing Toby Keith's signature blend of fun and energy in his music.

(Jeff Kravitz/ACMA2018/FilmMagic/Getty Images)

"Made in America"

"Made in America"
  • Released: 2011
  • Peak US Hot Country Songs (Billboard) Chart Position: #1
  • Peak US Billboard Hot 100 Chart Position: #40
  • Weeks on Chart: 19

"Made in America" is a patriotic country anthem that celebrates American values, traditions, and products. With its catchy melody and proud lyrics, the song resonates with audiences, embodying Toby Keith's signature blend of patriotism and musical prowess.

(Image via Show Dog-Universal Music)

"You Shouldn't Kiss Me Like This"

"You Shouldn't Kiss Me Like This"
  • Released: 2000
  • Peak US Hot Country Songs (Billboard) Chart Position: #1
  • Peak US Billboard Hot 100 Chart Position: #32
  • Weeks on Chart: 34

"You Shouldn't Kiss Me Like This" is a romantic country ballad that explores the thrill and temptation of a forbidden kiss. With its heartfelt lyrics and emotional delivery, the song captures the longing and desire of two people drawn to each other despite knowing they shouldn't indulge in their feelings. 

mariiaplo - stock.adobe.com

"A Little Less Talk and a Lot More Action"

"A Little Less Talk and a Lot More Action"
  • Released: 1993
  • Peak US Hot Country Songs (Billboard) Chart Position: #2
  • Weeks on Chart: 20

"A Little Less Talk and a Lot More Action" is a lively country tune that emphasizes the importance of action over empty promises, especially in relationships. With its catchy melody and straightforward lyrics, the song became a popular anthem for those seeking decisive action and commitment.

fasndee - stock.adobe.com

"I Wanna Talk About Me"

"I Wanna Talk About Me"
  • Released: 2001
  • Peak US Hot Country Songs (Billboard) Chart Position: #1
  • Peak US Billboard Hot 100 Chart Position: #28
  • Weeks on Chart: 28

"I Wanna Talk About Me" is a country song that humorously explores the dynamics of communication in relationships, with a focus on self-centered tendencies. Its catchy melody and relatable lyrics struck a chord with listeners, making it a chart-topping hit and a staple in Toby Keith's repertoire.

(MC2 Rebekah Blowers, USN, Public domain, via Wikimedia Commons)

"God Love Her"

"God Love Her"
  • Released: 2008
  • Peak US Hot Country Songs (Billboard) Chart Position: #1
  • Peak US Billboard Hot 100 Chart Position: #36
  • Weeks on Chart: 21

"God Love Her" is a country song that tells the story of a rebellious woman with a wild spirit and a penchant for danger. The song's driving rhythm and heartfelt lyrics capture the essence of a woman who lives life on her own terms, resonating with audiences for its relatable portrayal of independence and resilience.

(Lance Cpl. Ronald W. Stauffer, Public domain, via Wikimedia Commons)

"Who's Your Daddy?"

"Who's Your Daddy?"
  • Released: 2002
  • Peak US Hot Country Songs (Billboard) Chart Position: #1
  • Peak US Billboard Hot 100 Chart Position: #22
  • Weeks on Chart: 29

"Who's Your Daddy?" is a playful country song with catchy hooks and tongue-in-cheek lyrics about a man's confident swagger and charm. With its upbeat tempo and memorable chorus, the song became a chart-topping hit, showcasing Toby Keith's signature blend of humor and musical prowess.

(Image via DreamWorks)

"Red Solo Cup”

"Red Solo Cup”
  • Released: 2011
  • Peak US Hot Country Songs (Billboard) Chart Position: #9
  • Peak US Billboard Hot 100 Chart Position: #15
  • Weeks on Chart: 20

Even if you don't listen to country music, you have probably heard this song before. It was Keith's highest-charting single on non-country radio (peaking at #15). It's also one of his best-selling singles, being certified triple platinum (sales over 3 million units).

"Red Solo Cup” is a lighthearted country anthem celebrating the iconic red plastic cup often used at parties and gatherings. With its catchy melody and humorous lyrics, the song became a popular party sing-along, resonating with audiences for its fun and relatable theme.

(Ethan Miller/Getty Images Entertainment/Getty Images)

"American Soldier"

"American Soldier"
  • Released: 2003
  • Peak US Hot Country Songs (Billboard) Chart Position: #1
  • Peak US Billboard Hot 100 Chart Position: #28
  • Weeks on Chart: 23

"American Soldier" is a heartfelt tribute to the bravery and sacrifice of American soldiers serving their country. With poignant lyrics and a stirring melody, the song honors the dedication and resilience of those in the military, becoming an anthem of patriotism and gratitude.

(Spc. Aaron Rosencrans, Public domain, via Wikimedia Commons)

"I Love This Bar"

"I Love This Bar"
  • Released: 2003
  • Peak US Hot Country Songs (Billboard) Chart Position: #1
  • Peak US Billboard Hot 100 Chart Position: #26
  • Weeks on Chart: 24

"I Love This Bar" raises a glass to the simple joys of life found in a neighborhood bar. The song's upbeat melody and relatable lyrics pull you into the song so you almost feel like you are at the bar yourself as you sing along.

VTT Studio - stock.adobe.com

"How Do You Like Me Now?!"

"How Do You Like Me Now?!"
  • Released: 1999
  • Peak US Hot Country Songs (Billboard) Chart Position: #1
  • Peak US Billboard Hot 100 Chart Position: #31
  • Weeks on Chart: 43

"How Do You Like Me Now?!" is a defiant country song about achieving success and proving doubters wrong drawing a vivid picture as the singer reflects on his life which is in stark contrast to that of his high school crush. The song celebrates personal triumph and newfound confidence and became a signature hit for Toby Keith.

(Rick Diamond/Getty Images Entertainment/Getty Images)

"Beer for My Horses"

"Beer for My Horses"
  • Released: 2003
  • Peak US Hot Country Songs (Billboard) Chart Position: #1
  • Peak US Billboard Hot 100 Chart Position: #22
  • Weeks on Chart: 39

"Beer for My Horses" featuring Willie Nelson is a tongue-in-cheek song about individuals taking justice into their own hands for the sake of their town. The song paints a vivid picture of small-town law enforcement and community values coupled with a catchy melody and a memorable collaboration between two country music icons.

The song became so popular (and a signature song for Keith) that a film based on the song was released in 2008.

(Image via DreamWorks Records)

"As Good as I Once Was"

"As Good as I Once Was"
  • Released: 2005
  • Peak US Hot Country Songs (Billboard) Chart Position: #1
  • Peak US Billboard Hot 100 Chart Position: #28
  • Weeks on Chart: 23

"As Good as I Once Was" by Toby Keith is a country song that humorously reflects on aging and past experiences. The lyrics depict a protagonist who may not be as youthful or spry as before but still embraces life with gusto and resilience.

(Image via DreamWorks Records)

"Courtesy of the Red, White and Blue"

"Courtesy of the Red, White and Blue"
  • Released: 2002
  • Peak US Hot Country Songs (Billboard) Chart Position: #1
  • Peak US Billboard Hot 100 Chart Position: #25
  • Weeks on Chart: 22

Released in the wake of 9/11, "Courtesy of the Red, White and Blue" expresses unwavering support for the military and a willingness to defend American ideals. With its driving beat and passionate vocals, it became a rallying cry for many in the aftermath of the attacks.

(Official Navy Page from United States of America MC3 Christopher S. Johnson/U.S. Navy, Public domain, via Wikimedia Commons)

"Should've Been a Cowboy"

"Should've Been a Cowboy"
  • Released: 1993
  • Peak US Hot Country Songs (Billboard) Chart Position: #1
  • Peak US Billboard Hot 100 Chart Position: #93
  • Weeks on Chart: 23

"Should've Been a Cowboy" is a classic country song about a man who longs for the simplicity and lack of attachments that existed in the Old West. This song really hit home for a lot of country fans when it came out because it captures that nostalgic feeling of wanting to escape the daily grind and live a more rugged, free-spirited lifestyle. The song became Keith's debut single, as well as his first #1 hit on the US Billboard Hot Country Songs chart. It helped establish him as a prominent figure in country music.

(Image via Polygram/Mercury 864990)