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)
329.4K viewsJun 6, 2023
TikToktobykeithofficial
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)
21.5K viewsFeb 24, 2024
YouTubeACM - Academy of Country Music
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)
339.9K views8 months ago
YouTubeACM - Academy of Country Music
Downtown Avenue – Should've Been A Cowboy (by Toby Keith) | Live at Jason Aldean's, Las Vegas
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Downtown Avenue – Should've Been A Cowboy (by Toby Keith) | Live at Jason Aldean's, Las Vegas
9.2K views5 months ago
YouTubeDowntown Avenue
Downtown Avenue – Should've Been A Cowboy (by Toby Keith) | Live at Jason Aldean's, Las Vegas
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Downtown Avenue – Should've Been A Cowboy (by Toby Keith) | Live at Jason Aldean's, Las Vegas
4K views5 months ago
YouTubeDowntown Avenue
Toby Keith Performing Should've Been A Cowboy on 2004 on a Flip Phone camera! ‪@TobyKeith‬
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Toby Keith Performing Should've Been A Cowboy on 2004 on a Flip Phone camera! ‪@TobyKeith‬
1.2K views2 months ago
YouTubeNikLovesEditing
Downtown Avenue – Should've Been A Cowboy (by Toby Keith) | Live at Jason Aldean's, Las Vegas
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Downtown Avenue – Should've Been A Cowboy (by Toby Keith) | Live at Jason Aldean's, Las Vegas
1.6K views5 months ago
YouTubeDowntown Avenue
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Downtown Avenue – Should've Been A Cowboy (by Toby Keith) | Live at Jason Aldean's, Las Vegas
10.8K views5 months ago
YouTubeDowntown Avenue
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Should've Been A Cowboy - Toby Keith #tobykeith #shouldvebeenacowboy #countrylyrics #countrymusic #realcountrymusic
1.4K views1 month ago
TikTokrodeoradiolyrics
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Downtown Avenue – Should've Been A Cowboy (by Toby Keith) | Live at Jason Aldean's, Las Vegas
106 views6 months ago
YouTubeDowntown Avenue
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"Should've Been A Cowboy " - Toby Keith,#fun-music-videos,#90s-best-country-music-songs
654 views5 months ago
YouTubeWestrane Studios
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Downtown Avenue – Should've Been A Cowboy (by Toby Keith) | Live at Ole Red, Las Vegas
2.4K views6 months ago
YouTubeDowntown Avenue
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Should’ve Been a Cowboy Toby Keith (90s country song)
3.2K views1 month ago
TikTokkee9lan
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30 years ago today, #ShouldveBeenACowboy was released...and the rest is history. #TobyKeith #CountryMusic
306.9K viewsFeb 12, 2023
TikToktobykeithofficial
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Downtown Avenue – Should've Been A Cowboy (by Toby Keith) | Live at Ole Red, Las Vegas
2.2K views7 months ago
YouTubeDowntown Avenue
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"Should’ve Been a Cowboy" Toby Keith ‧ 1993 #countrymusic
1.7K views8 months ago
YouTubeDee🎶Ess
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Downtown Avenue–Should've Been A Cowboy (by Toby Keith) | Live at Oso Bear Point Harbor,Orange Beach
1.2K views7 months ago
YouTubeDowntown Avenue
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Downtown Avenue – Should've Been A Cowboy (by Toby Keith) | Live at Oso, Orange Beach
653 views6 months ago
YouTubeDowntown Avenue
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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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Downtown Avenue – Should've Been A Cowboy (by Toby Keith) | Live at Ole Red, Las Vegas
3K views6 months ago
YouTubeDowntown Avenue
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Downtown Avenue – Should've Been A Cowboy (by Toby Keith) | Live at Ole Red, Las Vegas
1.4K views7 months ago
YouTubeDowntown Avenue
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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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“i should’ve been a cowboy..” #TobyKeith #countrymusic
1.4K views6 months ago
YouTubeY'ALL BAND
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Wade Hayes performing acoustic version of Toby Keith's Should've been a cowboy 10/2025
913 views10 months ago
YouTubeJanet & Daniel's adventures & sights
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A young Toby Keith singing “Should’ve Been a Cowboy” in front of George Jones is about as country
1.9M views4 months ago
YouTubeDJ Pavinso
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First Time Listening to Toby Keith: A Reaction Video
3.5M views8 months ago
TikTokterryandkaniyia
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Should’ve Been A Cowboy#90sthrowback #90music #tobykeith #countrymusic #90song
1.6K views9 months ago
TikTokcountry_roads_90s
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Understanding 'Skiddadle' in Horse Riding Culture
3.1M viewsApr 28, 2025
TikToksocietycallsmesatan
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should’ve been a cow #boy @Toby Keith
2.7M viewsJul 16, 2022
TikTokthekillers
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Jelly Roll & T-Pain Cover Toby Keith's Classic Hit
1.4M viewsJun 2, 2024
TikTokfeel_good_music_
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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 views4 months ago
TikTok90scountrymusic8
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I Should’ve Been a Cowboy - The Most Played 90s Country Song
1.2M viewsFeb 9, 2024
TikTokdillon.weldon
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Exploring 'Should’ve Been A Cowboy' by Toby Keith
426.4K viewsMar 18, 2025
TikTokkountrykartt
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Honoring Toby Keith: Should've Been a Cowboy Tribute
890.5K viewsFeb 6, 2024
TikTokjustintaite
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Should’ve been a cowboy #tobykieth #rileygreen #shouldvebeenacowboy #rupparena #lexington #kentucky
2.1M viewsMar 9, 2024
TikTokjurry623
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Cowboy Butter Ravioli 🤠 I start by browning 1 pound of ground beef until it’s cooked through, then drain the grease. Add in your onion and garlic and cook until fragrant. You can add in your favorite seasonings, and of course, I use Kinder’s Cowboy Butter seasoning! Use whatever seasonings you prefer and adjust everything to your taste. Next, I add 1 can of tomato juice, 1 can of roasted tomatoes, and tomato paste. Let everything simmer until it’s cooked down, flavorful, and delicious. Give it
186.3K views3 weeks ago
TikTokbrkxdh
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Tayler Holder (@itstaylerholder)’s video of toby keith
678.7K viewsFeb 7, 2024
TikTokitstaylerholder
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a light day’s work #cowboy #cowgirl #cattledog #cattle #herdingdog | cow
169.1K views1 month ago
TikToklittlemisslolabear
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Tribute to Toby Keith: I Should've Been A Cowboy | Josh Weathers Cover
280.6K viewsFeb 6, 2024
TikTokjosh.weathers.official
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Honored to have sung “Should’ve Been A Cowboy” at the Toby Keith: American Icon Tribute. What a legend. Tune in tonight at 9/8c on @NBC and @Peacock.
174.3K viewsAug 28, 2024
TikToklukebryan
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Cowboy ? #tobykeith #ishouldofbeenacowboy @Toby Keith #singingdog #8
127.4K viewsOct 3, 2024
TikTokmitchapalooza
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Toby Keith ‘Should’ve Been A Cowboy’ (Story Behind The Song)
37.9K viewsAug 8, 2025
YouTubeAmerican Country Network
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I almost got trampled by a cow 🐄 Insert Tony Keith song here: “I should’ve been a cowboy” 🤠 #southernaccent #countryman #countryboy #cattle #farmlife
100.7K viewsApr 11, 2024
TikTokkeenanwilsonactor
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The Country Wire on Instagram: "Just two cowboys enjoying some good country music @tobykeith @troyaikman Toby Keith’s “Should’ve Been a Cowboy,” released in 1993, was his debut single and quickly became a signature song for both him and 1990s country music. It tells the story of a man daydreaming about living the adventurous life of an old Western cowboy instead of his ordinary reality. The lyrics reference classic cowboy icons like Gene Autry and Roy Rogers, tapping into nostalgia for simpler,
261K views11 months ago
Instagramthecountrywire
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Nostalgic Country Vibes: Should've Been a Cowboy
21.5K views7 months ago
TikToklucyandy69
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Carrie Underwood Should've Been a Cowboy Cover at BMI
114.7K viewsNov 9, 2022
TikToknotcarrieunderwood
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he’s convinced he should have been a cowboy💀 which one are you- team surfer or team cowboy??🤠 #texas #surfer #cowboy #southern
48.1K viewsJun 27, 2024
TikTokmeganbcall
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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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He should’ve been a COWBOY! #eskimojoes #bedlam #tobykeith
82.9K viewsJan 19, 2023
TikTokcadedean5
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Brooks & Dunn Pay Tribute to Toby Keith with "Should've Been a Cowboy" #shorts #countrymusic
14.7K viewsApr 29, 2024
YouTubeCountryLine
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RIP Toby Keith: Should’ve Been A Cowboy (1993) #shouldvebeenacowboy #tobykeith #riptobykeith #countrymusic #countryboy #countrygirl #countrymusictiktoks #90scountry
340.4K viewsApr 11, 2025
TikTokgreatest.songs.all.time
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Downtown Avenue – Should've Been A Cowboy (by Toby Keith) | Live at Jason Aldean's, Las Vegas
9K views5 months ago
YouTubeDowntown Avenue
1:59
Easy First Song to Learn on Guitar | Should've Been a Cowboy
16.8K viewsMay 5, 2025
YouTubeCountrySongTeacher
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Cowboy #fypシ #fyp #viraltiktok #viral #country | cowboy
11.1K views10 months ago
TikToklucamora02044xx
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Jelly Roll "Should've Been A Cowboy" Toby Keith Tribute LIVE: Billy Bob's Texas 5/14/24 Clip
33.5K viewsJun 26, 2024
YouTubeLiveFromFrisco
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Koe Wetzel Covers Toby Keith's
17.6K viewsJun 19, 2024
TikTokkeepingitcountry_
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I couldn’t believe the news! Toby Keith was a legend. #guitartok #musi...
36.4K viewsFeb 12, 2024
TikTokkainoahbowman
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Riley Green covering Toby Keith’s “Should’ve Been a Cowboy”
13.6K viewsAug 4, 2025
TikTokcountryconcertvideos
0:36
Luke Bryan sings Toby Keith's classic 'Should've Been A Cowboy' at concert celebrating Toby
22.9K viewsAug 29, 2024
YouTubeCountryLine
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Sorry fellas yall gotta tighten up😂#fyp #horse #caballostiktok #paratiiiiiiiiiiiiiiiiiiiiiiiiiiiiiii
6.2K views4 months ago
TikTokel_felipemora
0:59
Toby Keith Should've Been A Cowboy #shortsfeed #outlawcountry #countrymusic
6.1K views8 months ago
YouTubeCountry Music Spotlight
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RYEdio PT 175 “Should Been A Cowboy” @Toby Keith #tobykeith #cowboy
12.7K views10 months ago
TikTokryedavismusic
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Y'all been missing live music this year? #tobykeith #countrymusic #shouldvebeenacowboy #concert #livemusic #military
261.2K viewsDec 9, 2020
TikToktobykeithofficial
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Toby Keith vs YC: Should've Been a Cowboy Mashup
4.3K views6 months ago
TikTokcoltcorley5
0:08
Should’ve been a cowboy 🤠 #cowboy #country #countrymusic
33.4K viewsJul 29, 2022
TikTokmegpatrickmusic
0:58
Toby Keith Should've Been A Cowboy #liveandkickingmusic
13.2K viewsNov 8, 2024
YouTubeLive And Kicking Music
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Discover the Joy of Campfire Songs with Toby Keith
10.3K viewsMar 5, 2025
TikTokcountrysayings
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Story Behind the Song - Toby Keith ‘Should’ve Been A Cowboy’
18.3K viewsAug 1, 2025
YouTubeConman FM
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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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Should Have Been a Cowboy - Toby Keith Tribute
29.7K viewsMay 10, 2021
TikTokmatt_merrill
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