Toby Keith: ’90s Hits That Dominated The Decade

Toby Keith shot to country music fame in the 1990s with his emotional lyrics, deep voice, and slightly rough edges. Keith's debut hit, “Should've Been a Cowboy,” was just the song country music fans needed, especially at a time when country music was often tinged with pop.

Toby Keith's '90s chart dominance set him up for ongoing success, culminating in his induction into the Nashville Songwriters Hall of Fame in 2021 and the Country Music Hall of Fame in 2024, the year of his death. As well as helping shape the country music landscape for years to come, his work across the decade established him as a figure with strong opinions, genuine emotions, and a memorable talent. Join us as we look through these first years of Toby Keith's chart history and see where it all began.

In 1993, Keith signed with Mercury Records and released “Should've Been a Cowboy,” which spent 23 weeks on the Billboard Hot Country Songs chart, including two weeks at No. 1. This song, from his self-titled album, became the decade's most played country song on the radio.

After the success of “Should've Been a Cowboy,” Keith continued hitting the charts and thrilling fans. From his debut album came songs such as “He Ain't Worth Missing,” which peaked at No. 5 on the Billboard Hot Country Songs chart in 1993, “A Little Less Talk (And a Lot More Action),” which peaked at No. 2 in 1994, and “Wish I Didn't Know Now,” which also made it to No. 2 just three months later.

In 1994, Keith released his sophomore album, Boomtown, which was certified Gold by the Recording Industry Association of America (RIAA) later that year. The album included hits such as “Who's That Man,” which topped the Hot Country Songs chart in 1994, and 1995's “Big Ol' Truck,” which reached No. 15. Also in 1995, “You Ain't Much Fun” reached No. 2, and “Upstairs Downtown” peaked at No. 10.

By 1996, Keith was a major country music star with massive radio play, and his songs continued to hit the charts. In 1996, “Does That Blue Moon Ever Shine on You” made it to No. 2 on the Billboard Hot Country Songs chart, and “Me Too” hit No. 1, spending a total of 20 weeks on the chart.

Also in 1996, “A Woman's Touch” peaked at No. 6, and the following year, “We Were in Love” reached No. 2. In these mature songs, we hear a softer and more romantic side of Keith, with lyrics from “A Woman's Touch” including the lines, “What my heart needs is a woman's touch / A tender hand to fix it up / Its rough and ragged edges sure could use some love / What my heart needs is a woman's touch.”

Similarly, the wistful lyrics of “We Were in Love” include “I can still see you when I sleep / There is a picture I still keep / You with your hair in the wind / And me with that crazy grin / Under a summer sky / When dreams were too young to die.” Based on those chart positions, Keith's fans loved it all.

Keith's 1997 album Dream Walkin' received a Gold certification from the RIAA on March 26, 1998. Released with Mercury Records, this album featured hit songs such as the title track, “Dream Walkin',” which reached No. 5 on the Billboard Hot Country Songs chart in 1998, and “Double Wide Paradise,” which peaked at No. 40.

Other hits included “I'm So Happy I Can't Stop Crying,” where Keith duetted with the original artist, Sting. These and other self-penned songs defined Keith's country sound, with pedal steel guitar, acoustic guitar, a catchy beat, and emotional lyrics.

In 1998, Keith moved from Mercury Records to DreamWorks Nashville in search of greater creative control over his music. Before leaving Mercury, he released the album Greatest Hits Volume One, which he followed up in 1999 with How Do You Like Me Now?! “Getcha Some” from Greatest Hits Volume One reached No. 18 on the Billboard Hot Country Songs chart in 1998, and the title track from the studio follow-up, “How Do You Like Me Now?!,” peaked on March 18, 2000, at No. 1, where it stayed for five weeks.

All six of Keith's '90s albums and four of his singles went on to receive Gold and Platinum certifications from the RIAA, with plenty of later hits joining them. Keith's later successes include “Beer For My Horses,” recorded with Willie Nelson, which topped the Billboard Hot Country Songs chart in 2003 and stayed at No. 1 for six weeks. During the 2000s and beyond, Keith released 26 more albums, including his last, titled 100% Songwriter. This final album featured previous hits, allowing fans to look back on his remarkable career.

Keith entered the 2000s with a range of hits under his belt, and he didn't stop recording successful songs. In 2001, he was named the Country Music Association's male vocalist of the year, and across his career, he won three Billboard Music Awards and secured seven GRAMMY nominations.

Along with his hit single with Willie Nelson, Keith went on to top the charts with songs such as the aptly named “As Good as I Once Was,” which hit No. 1 on the Billboard Hot Country Songs chart in 2005 and stayed there for six weeks. He also gave back to his country, performing on several United Service Organization (USO) tours to entertain troops stationed abroad. Toby Keith's 1990s songs set him up for a life of success and also of gratitude, with charity becoming increasingly important to him.

While Keith continued to write and co-write chart-topping songs even after his stomach cancer diagnosis in 2021, the 1990s were the defining years of this country music powerhouse. His debut single, “Should've Been a Cowboy,” was such a defining song that Keith called his 2018 tour the Should've Been a Cowboy XXV Tour. That same year at the Academy of Country Music Awards, Keith teamed up with Blake Shelton to sing a version of the song that launched his career. If you're looking to join us in remembering Toby Keith, his 1990s breakthrough is the perfect place to start.