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Toby Keith's First #1 Hit: 'Should've Been a Cowboy' (1993)

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

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

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

FacebookToby Keith

Toby Keith & Blake Shelton - Should've Been A Cowboy (Live from the 53rd ACM Awards)

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

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)

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

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

Toby Keith — “Should've Been a Cowboy” Live

608 views4 weeks ago

TikTokkeepitcountryyall

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

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

Throwback Country - @Toby Keith Shoulda Been a Cowboy #nashvilleinthenortheast #getyourcountryon #shotofsouthern #countrymusic #countrygirl #country #music #tobykeith

2.5K viewsOct 3, 2024

TikTokshotofsouthern

Should've Been A Cowboy - Toby Keith #tobykeith #shouldvebeenacowboy #countrylyrics #countrymusic #realcountrymusic

1.4K views2 months ago

TikTokrodeoradiolyrics

Toby Keith performing I should've been a cowboy

1.4K views7 months ago

YouTubeIsaiah M

Toby Keith ‘Should’ve Been A Cowboy’ (Story Behind The Song)

37.9K viewsAug 8, 2025

YouTubeAmerican Country Network

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

Elijah Scott Sings Toby Keith & Cher Mashup: 'Shoulda Been A Cowboy x Believe'

182.7K viewsOct 26, 2025

TikTokelijahscottmusic

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

Should’ve Been a Cowboy Toby Keith

8.2K views9 months ago

YouTubeTheatrical Garbage

Downtown Avenue – Should've Been A Cowboy (by Toby Keith) | Live at Ole Red, Las Vegas

1.4K views8 months ago

YouTubeDowntown Avenue

Should Have Been a Cowboy by Toby Keith performed by Country Roads and Friends

1.4K views6 months ago

YouTubeNicole White Creative Consulting

Toby Keith - Should’ve been a cowboy by The Emo Cowboy on Broadway in Nashville

1K views8 months ago

YouTubeBrad Redlich

Easy First Song to Learn on Guitar | Should've Been a Cowboy

16.8K viewsMay 5, 2025

YouTubeCountrySongTeacher

"Should've Been a Cowboy" (cover) #countrymusic #tobykeith # #90scountry

1.3K views3 months ago

YouTubeRusty VanSickle

Toby Keith's classic Shoulda Been a Cowboy 🤠 #countrymusic #tobykeith #country #coversong

1.1K views3 months ago

YouTubeCowboy Cody

Oklahoma Just Did This for Toby Keith #shorts

3.1K views9 months ago

YouTubeCountry After Hours

My cover of Should've Been A Cowboy by Toby Keith

1.3K views1 month ago

YouTubeRyder Neeley

"Should’ve Been a Cowboy" Toby Keith ‧ 1993 #countrymusic

1.7K views9 months ago

YouTubeDee🎶Ess

Should’ve Been a Cowboy Toby Keith Song Live 2025 #countrymusic #livemusic

4K viewsJul 19, 2025

YouTubeMy Card Art

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

FacebookToby Keith

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