‘Should’ve Been a Cowboy’ Country Singer Was 62

Toby Keith, the country singer who scored the genre’s most-played song of the ’90s with “Should’ve Been a Cowboy,” died on Monday night of stomach cancer. He was 62.

The news was announced on Keith’s official website as well as his social media channels. “Toby Keith passed peacefully last night on Feb. 5, surrounded by his family,” the statement reads. “He fought his fight with grace and courage. Please respect the privacy of his family at this time.”

In June 2022, Keith revealed that he had been diagnosed with stomach cancer. “I’ve spent the last 6 months receiving chemo, radiation and surgery,” Keith wrote at the time. “So far, so good. I need time to breathe, recover and relax.”

Born in Clinton, Okla. on July 8, 1961, Keith started his career in music at the age of 20 by forming the Easy Money Band with his friends. In the mid-’80s, the group began playing at honky-tonks in Oklahoma and Texas, and by the ’90s Keith was husking in Nashville in hopes of getting a record deal. His big break finally came when a flight attendant gave his demo tape to Mercury Records exec Harold Shedd, who had worked with Shania Twain and Billy Ray Cyrus. Shedd signed Keith and released his 1993 debut single, “Should’ve Been a Cowboy,” which reached No. 1 on Billboard’s country songs chart. The song would go on to become the most-played country song of the decade.

The success of “Should’ve Been a Cowboy” continued with Keith’s self-titled debut album, which was certified platinum and produced three more hits: “He Ain’t Worth Missing,” “A Little Less Talk and a Lot More Action” and “Wish I Didn’t Know Now.”

Keith signed with Polydor Records to release his second album, “Boomtown,” in 1994. Its lead single, “Who’s That Man,” reached No. 1 on the country charts and the album was certified platinum. In 1995, Keith released his first Christmas album, “Christmas to Christmas.” Keith’s third album “Blue Moon” followed in 1996, reaching platinum status with single “Does That Blue Moon Ever Shine on You” peaking at No. 2. He returned to Mercury in 1997 and put out his fourth album “Dream Walkin’,” which scored two No. 2 songs, “We Were in Love” and a cover of Sting’s “I’m So Happy I Can’t Stop Crying,” on which Sting provided vocals and bass guitar. Keith ended his tenure at Mercury with 1998’s “Greatest Hits Volume One.”

In 1999, Keith moved to DreamWorks Records. His first single on the label, “When Love Fades,” performed poorly on the charts so he had it withdrawn and replaced by “How Do You Like Me Now?,” which became his first song to break through the top 40 on the Hot 100, peaking at No. 31. The album “How Do You Like Me Now?” was released later that year and produced another country No. 1 with “You Shouldn’t Kiss Me Like This.” His 2001 album “Pull My Chain” followed a similar trajectory, with all three singles — “I’m Just Talkin’ About Tonight,” “I Wanna Talk About Me” and “My List” reaching the top spot on the country charts.

2002’s “Unleashed” featured “Beer for My Horses,” a duet with Willie Nelson that topped the country charts for six weeks and made it to No. 22 on the Hot 100. In 2003, Keith dropped his eighth studio album, “Shock’n Y’all,” and all three singles — “I Love This Bar,” “American Soldier” and “Whiskey Girl” — reached No. 1 on the country charts. In 2004, Keith released his second “Greatest Hits” record, and in 2005 released his last album with DreamWorks, “Honkytonk University,” with single “As Good as I Once Was” hitting No. 1.

Keith’s rapid-fire success slowed a little after DreamWorks ceased operations and he started his own label, Slow Dog Nashville. His 2006 album, “White Trash With Money,” didn’t make as big of a splash, but 2007’s “Big Dog Daddy” saw his first No. 1 since 2005 with “Love Me if You Can.” “Big Dog Daddy” was followed by another Christmas album and greatest hits compilation, and two more hits-producing albums, 2008’s “That Don’t Make Me a Bad Guy” and 2009’s “American Ride.”

2010’s “Bullets in the Gun” was Keith’s first record that didn’t result in a top 10 hit. But Keith couldn’t dodge success for too long — 2011’s “Clancy’s Tavern” contained the No. 1 song “Made in America” and “Red Solo Cup,” Keith’s biggest crossover to date which peaked at No. 15 on the Hot 100.

Keith released three more albums over the next three years, “Hope on the Rocks,” “Drinks After Work” and “35 MPH Town.” He was inducted into the Songwriters Hall of Fame in 2015 and released a compilation record, “The Bus Songs,” in 2017.

In September 2023, Keith performed for the first time since his cancer diagnosis at the People’s Choice Country Awards, where he received the Country Icon Award.