Top 10 Toby Keith Songs

Toby Keith Songs

This Top 10 Toby Keith Songs list presents the best Toby Keith songs including “American Soldier,” “Red Solo Cup” and many more. Born and mostly raised in the state of Oklahoma in 1961, Toby Keith Covel quickly developed an interest in music after visits with his grandmother at her Billie Garner’s Supper Club in Fort Smith, Arkansas. In addition to his interest in music, he also played high school football. After graduation, Toby Keith worked in the oil fields until 1982 before unemployment routed his career path to a potential football career. Throughout this time frame, he did have a band he performed with but didn’t begin to focus on the pursuit of a music career until after he was unable to make the cut for the Oklahoma Outlaws football team of the United States Football League. At the time, Toby Keith and those closest to him weren’t so sure about his choice to pursue music as a career but it was something he enjoyed doing, so why not at least give it a try?

No More Doubts

The year 1984 saw Toby Keith’s decision to embark on a musical career begin to pay off in his favor when big band names began to play honky-tonk in the state of Oklahoma. By spring of 1993, Toby Keith released his self-titled debut album and it became certified platinum by the Recording Industry Association of America (RIAA) and gold with Music Canada. His second album, Boomtown, was released during the fall of 1994 and also became certified platinum by the RIAA. These two were followed in 1995 with the Christmas to Christmas album before 1996’s platinum-selling Blue Moon. 1997’s Dream Walkin’ earned Toby Keith RIAA gold while 1999’s How Do You Like Me Now? became his fourth platinum-certified seller to date.

Starting the year 2000, Toby Keith recorded and released three albums in a row that became at least double-platinum, starting with Pull My Chain in 2001, then Unleashed in 2002, and Shck’n Y’all in 2003. The majority of his number one singles come from these three albums. In total, Toby Keith has recorded and released twenty-one studio albums, seven compilation albums, sixty-nine singles, and fifty-four music videos. In addition to this impressive portfolio as a singer-songwriter, Toby Keith has also performed as an actor, specifically in 2006’s Broken Bridges and 2008’s Beer for My Horses.

Top 10 Toby Keith Songs

#10 – Who’s Your Daddy?

For Toby Keith, “Who’s Your Daddy?” became the first of his two biggest crossover hit singles as it peaked as high as number twenty-two on the US Billboard Hot 100, as well as number one on the US Billboard Hot Country Songs chart in 2002. From the album, Unleashed, Toby Keith narrated a comedic song about a young woman’s complicated romance with a considerably older man. Designed as a lighthearted, funloving single, “Who’s Your Daddy?” served as the inspirational spawn behind “Where’s Your Mommy?” by Cledus Judd in 2003.

#9 – God Love Her

Released in 2008 from the album, That Don’t Make Me a Bad Guy, “God Love Her” was Toby Keith’s country song tale of a preacher’s daughter saving his soul from the devil despite her own rebellious nature. True to Toby Keith’s form, “God Love Her” was a playful number siding more with comedy than seriousness. On the US Billboard Hot Songs chart, this RIAA-certified gold hit was a number one hit on the US Billboard Hot Country Songs chart and a number thirty-six hit on the US Billboard Hot 100.

#8 – Should’ve Been a Cowboy

The first single released by Toby Keith was “Should’ve Been a Cowboy,” which became his first number one hit on the US Billboard Hot Country Songs chart, as well as a crossover hit at number ninety-three on the US Billboard Hot 100. From the year it was released in 1993, it became the country song most requested and played throughout the decade of the 1990s and has since become certified gold by the RIAA. Playfully referencing the infamous cowboys from old wild west flicks, “Should’ve Been a Cowboy” has since become a staple song during sporting events at Oklahoma State University.

#7 – Red Solo Cup

“Red Solo Cup” was a comedic country single recorded and released by Toby Keith from his 2011 album, Clancy’s Tavern. Deliberately designed as a ridiculous take on the infamous red plastic cups by the brand, Solo, also has a remixed version on Keith’s 2012 album, Hope on the Rocks. This comedic country song performance of “Red Solo Cup” made references throughout the song of its popularity as an item used at parties and not just as something to drink beverages from.

Although this song may seem an unlikely number to succeed, it became a double-platinum seller with the RIAA and the biggest crossover hit Toby Keith ever had in his career. On the US Billboard Hot Country Songs chart, it peaked at number nine and was a number fifteen hit on the US Billboard Hot 100, therefore making this the best commercial to ever promote “Red Solo Cup” as a must-have product.

#6 – How Do You Like Me Now?

In November 1999, “How Do You Like Me Now?” became more than Toby Keith’s fourth number-one hit on the US Billboard Hot Country Songs chart. It topped that chart for five weeks and also became a number thirty-one hit on the US Billboard Hot 100. “How Do You Like Me Now?” earned nominations for Single of the Year and Song of the Year in 2001 with the Academy of Country Music Awards. Although it didn’t earn the win, it served as Keith’s big success story as the doubt once shared about making it in the entertainment industry was clearly eradicated after the release of this single. Delivered as a successful man addressing an old high school love interest who shunned him was the primary focus of this song, “How Do You Like Me Now?” also became the second certified gold hit from the RIAA for Keith.

#5 – American Soldier

Written and released in 2003, “American Soldier” came from Toby Keith’s album, Shock’n Y’all, and it became a number one hit on the US Billboard Hot Country Songs chart and a number twenty-eight hit on the US Billboard Hot 100. Born and raised as a patriot, Toby Keith paid homage to the men and women of the armed forces who serve the United States of America. The inspiration for “American Soldier” came after Keith met with the troops of the military when he had the good fortune to perform for them in base concerts.

#4 – I Love This Bar

“I Love This Bar” became yet another number one hit for Toby Keith after it was released as a single in 2003 from his album, Shock’n Y’all. It was also a number twenty-six hit on the US Billboard Hot 100 and became an RIAA certified gold seller. Singing in appreciation of a drinking establishment near and dear to Keith’s heart as a narrator, this song became the inspiration behind the restaurant chain, I Love This Bar & Grill. The first location popped up in Oklahoma City, Oklahoma where Toby Keith personally opened. These guitar-shaped restaurants specialize in southern-style cooking as part of their classic American cuisine and have multiple locations scattered throughout the U.S.

#3 – Beer for My Horses (featuring Willie Nelson)

In 2003, Toby Keith and Willie Nelson teamed up to perform “Beer for My Horses,” an RIAA-certified platinum single which saw the two men lyrically sharing their distaste of the current legal system where too many criminals get away with all the wrongdoings committed as opposed to an era where no crime was left unpunished. It became one of Toby Keith’s best-known hits as it topped the US Billboard Hot Country Songs chart for six weeks, as well as tying “Who’s Your Daddy?” as his highest-charted song on the US Billboard Hot 100 at number twenty-two. “Beer for My Horses” was also a source of comedic inspiration for the 2008 movie of the same title which saw Toby Keith co-star with Rodney Carrington.

#2 – As Good as I Once Was

“As Good as I Once Was” was a single that spent six weeks at the top of the US Billboard Country Songs chart after it was released in 2005. This reflective song of a middle-aged man sitting at a bar saw Toby Keith lyrically pour out his soul as he figures the best days of his life are now behind him. From the album, Honkytonk University, this RIAA-certified platinum single witnessed the vulnerable side to Toby Keith, which was a stark contrast from the considerably more aggressive “Courtesy of the Red, White and Blue” and its album, Unleashed. “As Good as I Once Was” still saw the comedic side of Keith as he pointed out the differences between energetic youth and worn-out adults.

#1 – Courtesy of the Red, White and Blue

September 11, 2001’s terrorist attacks sparked the patriot within Toby Keith to record and release the single, “Courtesy of the Red, White and Blue.” This occurred just months after his father, Hubert Keith Covel, was killed in a car accident on March 24. The song’s reference to the war in Afghanistan became a controversy when the Dixie Chicks voiced criticism against it and their opinion of George W. Bush. At first, Toby Keith was reluctant to record the song, opting to perform it only before the American troops. However, the military insisted Keith record and publicly release “Courtesy of the Red, White and Blue” as a patriot of the American people.

This song served as a key source of inspiration among supporters of the United States military at the time it was first released and continues to be a patriotic favorite to this day. It was actually the final song played in Baghdad, Iraq before the American troops pulled out to return home. The song was popular enough to also become the first of four singles from Toby Keith to become certified platinum by the RIAA. On the music charts, “Courtesy of the Red, White and Blue” peaked at number one on the US Billboard Country Songs chart and at number twenty-five on the US Billboard Hot 100.

Feature Photo: Spc. Aaron Rosencrans, Public domain, via Wikimedia Commons

Top 10 Toby Keith Songs article published on Classic RockHistory.com© 2022

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