Who's ready for the Should've Been a Cowboy XXV Tour, kicking off May 27? For the best seats in the house, get your tickets now! tobykeith.co/TKcowboy25 #TKCowboy25 | Toby Keith

Toby Keith - Should've Been a Cowboy | All Things Country

Check out the new live video for “Should’ve Been A Cowboy." The video features dozens of clips from live performances, including several from Toby's 11 USO tours, in celebration of the 25th anniversary of the song that started it all. #TKCowboy25 | Toby Keith

25 years ago, Toby's debut single “Should’ve Been A Cowboy” hit the airwaves. The song became his first #1 and established him as one of country’s most prolific songwriters by becoming the most played song of the 1990’s. Toby wrote 8 of the 10 songs on the album that started it all, which has been remastered and paired with 3 unreleased tracks written by Toby between 1986 and 1990. The album is out Nov. 30. Pre-order with exclusive merch only at Toby’s store: https://UMe.lnk.to/ShouldveBeenACowb

Toby Keith Should've Been a Cowboy Live Video 1993 Toby Keith Should've Been a Cowboy Lyrics [Verse 1] I'll bet you've never heard ol' Marshal Dillon say "Miss Kitty, have you ever thought of runnin' away Settlin' down, would you marry me If I asked you twice and begged you pretty please?" She'd have said yes in a New York minute They never tied the knot, his heart wasn't in it He just stole a kiss as he rode away He never hung his hat up At Kitty's place [Chorus] I should've been a cowboy I sho