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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.

More to come…

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