Toby Keith's Top 20 Billboard Hits

Toby Keith, the iconoclastic country singer, songwriter and singer of hits such as “Should've Been a Cowboy,” “American Soldier” and “Red Solo Cup,” died Feb. 5 at age 62. after a battle with stomach cancer.

Since his career debut in 1993, Keith has scored 20 number one hits Advertising signHot Country Songs Chart. Born in 1961, the Oklahoma native worked in the oil fields alongside his father after graduating from high school. He also started the Easy Money Band and began playing small clubs around Oklahoma and Texas. In the early 1990s, Keith moved to Nashville to pursue 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 penned by Keith, reached No. 1 on the Hot Country Songs chart, while his self-titled debut album was certified 4 times 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. Starting with “How Do You Like Me Now?!” of 1999, Keith's image and song choices began to change, embracing an in-your-face swagger and braggadocio, along with novelty-oriented songs like “Who's Your Daddy?” In 2001, inspired both by 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 outrage felt by many Americans, and also garnered backlash. Shortly thereafter, he would release “American Soldier,” which depicted the daily sacrifices of military personnel.

Keith founded the Show Dog Nashville label in 2005 and released his album White trash with money in 2006, scoring five top Country Songs hits from the album, including “A Little Too Late.” He went on to score hits with patriotic songs like “Made in America” ​​and “American Ride.” In 2011, another breakthrough song, “Red Solo Cup”, gave Keith his highest-charting song on the all-genre Billboard Hot 100, peaking at No. 15.

Keith won three Billboard Music Awards during his career and was named the Country Music Association's Top Vocalist in 2001. He won 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 2022 BMI Icon and won the BMI Songwriter of the Year award three times.

From 2002 to 2013, he also participated in 11 USO tours, performing for active duty service members in more than 15 countries. He also supported organizations such as his own Toby Keith Foundation, as well as Ally's House (an Oklahoma organization dedicated to helping children with cancer) and the OK Kids Korral, a no-cost home for families of children battling illnesses.

In October, boosted by his performance at 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 singer, hit maker, heartfelt songwriter, ardent, outspoken American military supporter and entrepreneur that was Toby Keith, Advertising sign recounts his 20 biggest hits on the Hot Country Songs charts.

Toby Keith's eldest Advertising sign Chart is based on actual performance on the weekly Hot Country Songs chart through the chart dated February 10, 2024. Songs are ranked on a reverse point system, with weeks at No. 1 earning the most and weeks at the lowest positions to earn less. Due to changes in chart methodology over the years, seasons are weighted to account for different chart turnover rates in different periods.