The hit started his run of 20 Hot Country Songs leaders.
On June 5, 1993, Toby Keith’s “Should’ve Been a Cowboy” jumped 4-1 on Billboard‘s Hot Country Songs chart, scoring its first of two weeks at the summit.
Keith penned the song himself, weaving in lyrics that romanticize old western movies and name-checking outlaw Jesse James and Gunsmoke characters Miss Kitty and Marshal Dillon. Having written or co-written the bulk of his hits, he was inducted into the Songwriter’s Hall of Fame in 2015.
Born in Clinton, Okla., Keith made his first of 74 Hot Country Songs appearances to date with the single, starting a history that includes 20 No. 1s among 42 top 10s. He’s also rolled up 10 No. 1s among 23 top 10s on Top Country Albums, most recently reaching the top 10 with The Bus Songs in 2017.
Fun fact regarding “Cowboy”: The song has been piped through loudspeakers at sporting events for years. In December 1993, Keith performed it during halftime at Texas Stadium, where the Dallas Cowboys were hosting longtime rivals the Washington Redskins. Was the home team inspired? The Cowboys romped to a 38-3 win.