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)
327.7K 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
Remember This One? Toby Keith - Should Have Been a Cowboy
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Remember This One? Toby Keith - Should Have Been a Cowboy
1.2K viewsSep 18, 2024
YouTubeUnforgettable Country
Should've Been A Cowboy 🤠 🗓️ 2018 | Toby Keith Blake Shelton #ACMawards | ACM - Academy of Country Music
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Should've Been A Cowboy 🤠 🗓️ 2018 | Toby Keith Blake Shelton #ACMawards | ACM - Academy of Country Music
1.8M views10 months ago
FacebookACM - Academy of Country Music
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
Luke Bryan sings Toby Keith's classic 'Should've Been A Cowboy' at concert celebrating Toby
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Luke Bryan sings Toby Keith's classic 'Should've Been A Cowboy' at concert celebrating Toby
22.9K viewsAug 29, 2024
YouTubeCountryLine
Should’ve Been a Cowboy Toby Keith Song Live 2025 #countrymusic #livemusic
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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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Jason Aldean - "Should've Been A Cowboy" Tribute to Toby Keith (Live from the 59th ACM Awards)
63.9K viewsMay 17, 2024
YouTubeACM - Academy of Country Music
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"Should’ve Been a Cowboy" Toby Keith ‧ 1993 #countrymusic
1.7K views9 months ago
YouTubeDee🎶Ess
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Toby Keith- Should've been a cowboy Lyrics
1.5K viewsOct 23, 2024
YouTubeNikLovesEditing
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Toby Keith performing I should've been a cowboy
1.4K views6 months ago
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Should've Been A Cowboy (Apple Music Sessions) - Riley Green: Song Lyrics, Music Videos & Concerts
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shazam.com
Toby Keith - Should’ve Been a Cowboy Lyrics & Meaning
Jun 16, 2009
songlyrics.com
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I Should've Been a Cowboy | '90s Country
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YouTubeCasa Mañana
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Toby Keith- Should've been a cowboy (half of the lyrics)
1.1K viewsOct 29, 2024
YouTubeNikLovesEditing
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I Should’ve Been a Cowboy - The Most Played 90s Country Song
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TikTokdillon.weldon
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Shoulda Been a Cowboy by Riley Green and Ella Langley - Country Music Duet
532.6K viewsNov 15, 2024
TikTokrileyduckman
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Elijah Scott Sings Toby Keith & Cher Mashup: 'Shoulda Been A Cowboy x Believe'
182.7K views11 months ago
TikTokelijahscottmusic
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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 views11 months ago
Instagramcountryrebel
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Story Behind the Song - Toby Keith ‘Should’ve Been A Cowboy’
18.4K viewsAug 1, 2025
YouTubeConman FM
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🎸Rusty Meyers sings "Should’ve Been a Cowboy" by Toby Keith🤠
2.7K viewsNov 26, 2024
YouTubeRusty Meyers
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Toby Keith - Should've Been a Cowboy | Story Behind the Lyrics
1K viewsMar 29, 2025
YouTubeWhiskey Dirt Road
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I should’ve been a cowboy #sunset #lyrics #countrymusic
299 views1 month ago
YouTubeSpadez444🕊️
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Should’ve been a cowboy #countrymusic #music #singing 
20.3K views11 months ago
YouTubeElijah Scott
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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 Toby Keith
8.2K views8 months ago
YouTubeTheatrical Garbage
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Should've Been A Cowboy | Toby Keith | 4 Chord Easy Guitar Songs
3.9K viewsOct 11, 2024
YouTubeCountrySongTeacher
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Should’ve Been a Cowboy – Full Guitar Lesson 🎸 (Easy Country – 3 Chords
1K views6 months ago
YouTubeDude named Wes
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A young Toby Keith singing “Should’ve Been a Cowboy” in front of George Jones is about as country as it gets 🤠 #TobyKeith #GeorgeJones #CountryMusic #90sCountry #ShouldveBeenACowboy
201.6K views5 months ago
TikTok90scountrymusic8
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Toby Keith - Should’ve been a cowboy by The Emo Cowboy on Broadway in Nashville
1K views7 months ago
YouTubeBrad Redlich
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Nostalgic Country Vibes: Should've Been a Cowboy
21.5K views7 months ago
TikToklucyandy69
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“i should’ve been a cowboy..” #TobyKeith #countrymusic
1.4K views6 months ago
YouTubeY'ALL BAND
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First Time Listening to Toby Keith: A Reaction Video
3.5M views9 months ago
TikTokterryandkaniyia
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Should Have Been A Cowboy solo 12.19.25 #pedalsteelguitar #countrymusic #livemusic
1.5K views9 months ago
YouTubeCzBMusic
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More #90scountrymusic dances! Should’ve Been a Cowboy has always been a faborite song of mine! Dance: Rope and Ride Choreography: Lynn Card Song: Should’ve Been a Cowboy by Toby Keith 32 count, 2 wall, #beginnerlinedance no tags, no restarts. Have fun with this one! #tobykeith #linedancing #countrygirl #linedancersoftiktok #flatbedlinedancing #cowgirlsoftiktok #countrydance #cowgirllinedance #cowgirlboots #dodgetruck #redcowgirlboots #shouldabeenacowboy #shouldvebeenacowboy #ropeandride
12.6K viewsJun 24, 2024
TikTokflatbedlinedancer
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Robert's Performance of Shoulda Been a Cowboy
11K viewsOct 19, 2024
TikTokdynamicsoundhouston
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Learn Guitar with Toby Keith's 'Should Have Been a Cowboy'
1.7K viewsMay 5, 2025
TikTokcountrysongteacher
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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
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Should’ve Been a Cowboy Toby Keith (90s country song)
3.2K views1 month ago
TikTokkee9lan
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Play "Should've Been A Cowboy" by Toby Keith with this simple "sliding E chord" method. #guitar #countrysongteacher #mattmccoy #guitarlesson https://countrysongteacher.com | Country Song Teacher
28.4K viewsSep 22, 2025
FacebookCountry Song Teacher
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Toby Keith's First #1 Hit: 'Should've Been a Cowboy' (1993)
329.5K viewsJun 6, 2023
TikToktobykeithofficial
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A Little Less Talk And A Lot More Action
4.3M viewsNov 29, 2018
YouTubeToby Keith - Topic
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should’ve been a cowboy 🤠 #sanantonio #ncaamusicfestival #marchmadness #jellyroll #tpain #tobykeith
931 viewsApr 7, 2025
TikToksanmarcossundaze
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Should’ve Been A Cowboy - Toby Keith: A Country Classic
894 viewsSep 21, 2025
TikTokgraysoncrainmusic
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Riley Green live: Should've Been a Cowboy — 06-18-26 performance
2.5K views3 months ago
TikToklabrujaa3
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should've been a cowboy -toby keith#music#usa#fyp#country | Country Music
1.2K views5 months ago
TikTokahmadayakobi
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Shoulda been a Cowboy | Redfeather live at National Tractor Pulls 2026
597 views1 month ago
YouTubeJoshua John
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Jelly Roll Singing Should've Been a Cowboy
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YouTubeBrandon Mitchell
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A Great Tribute To Toby Keith Should've Been A Cowboy By Brooks And Dunn At CMT 2024 #brooksanddunn #shouldvebeenacowboy #tobykeith #tribute #countrymusicug #hudsonjosephsr #keepingupwithlwetutes #jezreelhudsonjnr #hudsonjosephsnr #
18.2K viewsApr 10, 2024
TikTokhudsonjosephsnr
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A Tribute to Toby Keith: Should’ve Been A Cowboy
8.9K views7 months ago
TikTokdavisholl7
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should of been a cowboy!!.. song is released everywhere.
10 views2 months ago
YouTubeGood Ol' Boyz
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Chancey Williams shares amazing story of getting to sing “should have been a cowboy” with friend and country music legend, Toby Keith in front of 20,000 people at the rodeo #rodeo #cheyenne #tobykeith #riptobykeith #countrymusic #countrymusicfans #countrylegend #country #countrysinger #cheyennewyoming #cowboyshit #cowboyup | The Jarrod Morris Vibe
19.1K views11 months ago
FacebookThe Jarrod Morris Vibe
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Should've Been a Cowboy by Toby Keith Official
17K viewsJan 6, 2021
TikTokalyssa.capps
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🎵 should’ve been a cowboy 🎵 #coversong #TobyKeith #acappella #countrymusic
421 views1 month ago
YouTubeRollin’ Dawg Country
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cover song of should’ve been a cowboy by Toby Keith 
1.1K views4 months ago
YouTubeT-ChOrD
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Shoulda been a cowboy 🤠🤠 #shouldabeenacowboy #officeview #livemusic #teamTG #tylergarrett #viral #cover Thank you @jameefrench for having us! | Tyler Garrett
729 viewsSep 21, 2025
FacebookTyler Garrett
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Toby Keith | Should've Been A Cowboy (2024 Cover)
1.2K viewsFeb 26, 2024
YouTubeShane For Short
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Countrynews on Instagram: "Follow (us) @countrynews if you’re a true fan of country music! 😎 Toby Keith’s “Should’ve Been a Cowboy” stands as one of the most iconic debut singles in country music history, launching his career in 1993 with the swagger and storytelling that would define him for decades. The song blends nostalgia, humor, and Western romance, painting a picture of a man who dreams of living the cowboy life—riding the range, chasing adventure, and embodying the spirit of old-school
176.3K views10 months ago
Instagramcountrynews
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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
16.7K viewsNov 2, 2018
FacebookToby Keith
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Shoulda been a Cowboy - by the legend Toby Keith #tobykeith #shouldabeenacowboy #music #singing #cover #fyp #EllieMae #cowboy #idaho #countrymusic
8 months ago
TikTokelliemaemillenkamp
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I Should’ve Been a Cowboy was the most played song of the 90’s. #tobykeith #ishouldvebeenacowboy #90scountry #countrymusic | Dillon Weldon
1.1M viewsFeb 9, 2024
FacebookDillon Weldon
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Singin’ those campfire songs, woah I should’ve been a cowboy… #TobyKeith #countrymusic | Country Sayings
52.1K views11 months ago
FacebookCountry Sayings
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My cover of Should've Been A Cowboy by Toby Keith
1.3K views1 month ago
YouTubeRyder Neeley
“Should’ve Been a Cowboy” is the breakthrough song that launched Toby Keith into country music stardom. Released in 1993 as his debut single, the song captures the universal daydream of trading everyday life for the freedom and adventure of the Old West. Its meaning is rooted in nostalgia, imagining a simpler, bolder life filled with wide-open spaces, campfires, and cowboy heroes. The song was written by Toby Keith along with Chuck Cannon, inspired by their shared love for Western imagery and cl
10 months ago
Facebook
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I covered should've been a cowboy...
14.8K views6 months ago
YouTubeDrew Baldridge
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Shoulda Been a Cowboy: Embrace the Rodeo Spirit
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TikTokmaizy.abbott
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Shoulda Been A Cowboy | Dirty Prescott Kids
3.9K viewsMay 22, 2025
FacebookDirty Prescott Kids
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Shoulda been a cowboy fr fr
2.2K viewsAug 1, 2025
TikTokkenny.mooree
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What song gets you going on the dance floor? 🕺🏼 Follow @greatcountrymusic for more ❤️ Should’ve Been a Cowboy - Toby Keith Released in 1993 as the debut single from his self-titled album, this song quickly became a defining anthem of ‘90s country music and solidified Keith’s place as a major force in the genre. “Should’ve Been a Cowboy” captures the wistful longing for the freedom and adventure of the Old West. The song’s lyrics reflect a romanticized view of cowboy life, with lines like, “I s
3.5K viewsAug 10, 2024
FacebookCountry Music | Country Songs | Country Singers
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Dance to Country Music: Should’ve Been a Cowboy
1.6K views8 months ago
TikTokgebs_hart
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