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Toby Keith's First #1 Hit: 'Should've Been a Cowboy' (1993)
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Toby Keith's First #1 Hit: 'Should've Been a Cowboy' (1993)
329.5K viewsJun 6, 2023
TikToktobykeithofficial
The album that started it all! Should’ve Been A Cowboy (25th Anniversary Edition) has been remastered and features 3 rare songs from Toby’s personal vault. Listen now! https://UMe.lnk.to/ShouldveBeenACowboyGU | Toby Keith
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The album that started it all! Should’ve Been A Cowboy (25th Anniversary Edition) has been remastered and features 3 rare songs from Toby’s personal vault. Listen now! https://UMe.lnk.to/ShouldveBeenACowboyGU | Toby Keith
62.4K viewsNov 29, 2018
FacebookToby Keith
Should’ve Been A Cowboy (25th Anniversary) is out now. Here’s a throwback to the song that started it all! Listen to the new remastered version of “Should’ve Been A Cowboy” and | Toby Keith
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Should’ve Been A Cowboy (25th Anniversary) is out now. Here’s a throwback to the song that started it all! Listen to the new remastered version of “Should’ve Been A Cowboy” and | Toby Keith
Nov 30, 2018
FacebookToby Keith
Toby Keith & Blake Shelton - Should've Been A Cowboy (Live from the 53rd ACM Awards)
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Toby Keith & Blake Shelton - Should've Been A Cowboy (Live from the 53rd ACM Awards)
344.5K views9 months ago
YouTubeACM - Academy of Country Music
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
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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
305.9K views11 months ago
FacebookWhen The Cowboy Sings And Country Music One
ACM Rewind ⏪ #TobyKeith & #BlakeShelton - "Should've Been A Cowboy" (Live from the 53rd ACM Awards)
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ACM Rewind ⏪ #TobyKeith & #BlakeShelton - "Should've Been A Cowboy" (Live from the 53rd ACM Awards)
21.9K viewsFeb 24, 2024
YouTubeACM - Academy of Country Music
Hear “Should’ve Been A Cowboy” and over a dozen of Toby’s hits he wrote solo on his 100% Songwriter album! | Toby Keith
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Hear “Should’ve Been A Cowboy” and over a dozen of Toby’s hits he wrote solo on his 100% Songwriter album! | Toby Keith
4.6K viewsJan 3, 2024
FacebookToby Keith
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Toby Keith — “Should've Been a Cowboy” Live
608 views4 weeks ago
TikTokkeepitcountryyall
0:56
A young Toby Keith singing “Should’ve Been a Cowboy” in front of George Jones is about as country
2.3M views5 months ago
YouTubeDJ Pavinso
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Toby would be proud Jason Aldean ❤️ 🎥 Jason Aldean pays tribute to the late Toby Keith with a beautiful rendition of "Shoulda Been A Cowboy at the ACM Awards. | CountryLine
363.2K viewsMay 17, 2024
FacebookCountryLine
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Throwback Country - @Toby Keith Shoulda Been a Cowboy #nashvilleinthenortheast #getyourcountryon #shotofsouthern #countrymusic #countrygirl #country #music #tobykeith
2.5K viewsOct 3, 2024
TikTokshotofsouthern
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Should've Been A Cowboy - Toby Keith #tobykeith #shouldvebeenacowboy #countrylyrics #countrymusic #realcountrymusic
1.4K views2 months ago
TikTokrodeoradiolyrics
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Toby Keith performing I should've been a cowboy
1.4K views7 months ago
YouTubeIsaiah M
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Toby Keith ‘Should’ve Been A Cowboy’ (Story Behind The Song)
37.9K viewsAug 8, 2025
YouTubeAmerican Country Network
1:01
Story Behind the Song - Toby Keith ‘Should’ve Been A Cowboy’
18.4K viewsAug 1, 2025
YouTubeConman FM
Toby Keith - Should’ve Been a Cowboy Lyrics & Meaning
Jun 15, 2009
songlyrics.com
0:59
Elijah Scott Sings Toby Keith & Cher Mashup: 'Shoulda Been A Cowboy x Believe'
182.7K viewsOct 26, 2025
TikTokelijahscottmusic
1:25
Country Rebel on Instagram: "#Throwback to 1994, when @TobyKeith played his new song, “Should’ve Been A Cowboy,” for the then quarterback of the Dallas Cowboys, Troy Aikman. The song, he jokes, is what “took us off hamburger and put us on T-Bone.” Fun Fact: Troy went on to release a song with Toby titled “Two Pairs of Levis” in 1996. #TobyKeith #DallasCowboys #NFLCountry"
108.9K viewsOct 23, 2025
Instagramcountryrebel
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Should’ve Been a Cowboy Toby Keith
8.2K views9 months ago
YouTubeTheatrical Garbage
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Downtown Avenue – Should've Been A Cowboy (by Toby Keith) | Live at Ole Red, Las Vegas
1.4K views9 months ago
YouTubeDowntown Avenue
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Should Have Been a Cowboy by Toby Keith performed by Country Roads and Friends
1.4K views6 months ago
YouTubeNicole White Creative Consulting
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Toby Keith - Should’ve been a cowboy by The Emo Cowboy on Broadway in Nashville
1K views8 months ago
YouTubeBrad Redlich
1:59
Easy First Song to Learn on Guitar | Should've Been a Cowboy
16.8K viewsMay 5, 2025
YouTubeCountrySongTeacher
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"Should've Been a Cowboy" (cover) #countrymusic #tobykeith # #90scountry
1.3K views3 months ago
YouTubeRusty VanSickle
0:39
Toby Keith's classic Shoulda Been a Cowboy 🤠 #countrymusic #tobykeith #country #coversong
1.1K views3 months ago
YouTubeCowboy Cody
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Oklahoma Just Did This for Toby Keith #shorts
3.1K views9 months ago
YouTubeCountry After Hours
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My cover of Should've Been A Cowboy by Toby Keith
1.3K views1 month ago
YouTubeRyder Neeley
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"Should’ve Been a Cowboy" Toby Keith ‧ 1993 #countrymusic
1.7K views9 months ago
YouTubeDee🎶Ess
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Should’ve Been a Cowboy Toby Keith Song Live 2025 #countrymusic #livemusic
4K viewsJul 19, 2025
YouTubeMy Card Art
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The album that started it all! Should’ve Been A Cowboy (25th Anniversary Edition) is out November 30: remastered, featuring 3 rare songs from Toby’s vault, and available for pre-order now | Toby Keith
Oct 12, 2018
FacebookToby Keith
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