Toby Keith’s 20 Biggest Billboard Hits

Toby Keith, the iconoclastic country music singer, songwriter and hitmaker behind songs including “Should’ve Been a Cowboy,” “American Soldier” and “Red Solo Cup,” died Feb. 5 at age 62, following a battle with stomach cancer.

Since his career debut in 1993, Keith lobbed 20 songs to the pinnacle of Billboard‘s Hot Country Songs chart. Born in 1961, the Oklahoma native worked in the oil fields alongside his father after he graduated from high school. He also launched the Easy Money Band and began playing small clubs around Oklahoma and Texas. In the early 1990s, Keith moved to Nashville to continue pursuing music. After Keith’s demo tape was given to producer Harold Shedd, Keith signed a deal with Mercury Records.

His first hit came in 1993, when “Should’ve Been a Cowboy,” a solo write from Keith, hit No. 1 on the Hot Country Songs chart, while his eponymous debut album was certified 4x multi-platinum by the RIAA. His early career hits were marked by ballads that showcased his strong baritone and emotional range, such as “He Ain’t Worth Missin'” and “Who’s That Man,” as well as the romantic “Me Too.”

In 1998, seeking greater creative control, Keith left Mercury for DreamWorks Nashville. Beginning with 1999’s “How Do You Like Me Now?!,” Keith’s image and song selections began to shift, embracing an in-your-face swagger and braggadocio, along with more novelty-oriented songs such as “Who’s Your Daddy?” In 2001, inspired by both the loss of his father and the 9/11 attacks, Keith released “Courtesy of the Red, White & Blue (The Angry American),” with the controversial line “We’ll put a boot in your a–/ It’s the American way,” which both underscored the rage that many Americans felt, but also garnered garnered backlash. Not long after, he would release “American Soldier,” which depicted the everyday sacrifices of military personnel.

Keith co-founded the label Show Dog Nashville in 2005 and released his album White Trash With Money in 2006, earning top five Country Songs hits from the album including “A Little Too Late.” He continued scoring hits patriotic-themed songs such as “Made in America” and “American Ride.” In 2011, another novelty song, “Red Solo Cup,” gave Keith his highest-charting song on the all-genre Billboard Hot 100, reaching No. 15.

Keith won three Billboard Music Awards during his career, and was named the Country Music Association’s male vocalist of the year in 2001. He earned the ACM’s Merle Haggard Spirit Award, and was inducted into both the Songwriters Hall of Fame and the Nashville Songwriters Hall of Fame. He was named a BMI Icon in 2022, and won BMI’s country songwriter of the year honor three times.

From 2002-2013, he also went on 11 USO tours, performing for active-duty service members in over 15 countries. He also supported organizations including his own Toby Keith Foundation, as well as Ally’s House (an Oklahoma organization dedicated to aiding children with cancer), and the OK Kids Korral, a cost-free home for families of children battling illness.

In October, bolstered by his performance on the inaugural People’s Choice Country Awards, Keith’s “Don’t Let the Old Man In” topped the Country Digital Song Sales chart.

As the world remembers the burly-voiced singer, the hitmaker, the heartfelt songwriter, the staunch, outspoken American military supporter, and businessman that was Toby Keith, Billboard recounts his 20 biggest Hot Country Songs chart hits.

Toby Keith’s Biggest Billboard Hits chart is based on actual performance on the weekly Hot Country Songs chart through the list dated Feb. 10, 2024. Songs are ranked based on an inverse point system, with weeks at No. 1 earning the greatest value and weeks at lower ranks earning less. Due to changes in chart methodology over the years, eras are weighted to account for different chart turnover rates over various periods.