3:30 Toby Keith - Should've Been A Cowboy (Official Music Video) 4:02 Toby Keith - Should've Been A Cowboy 5:26 Toby Keith - Should've Been a Cowboy Live XXV 2:52 Jelly Roll feat. T-Pain – Should’ve Been a Cowboy (Amazon Music Original) 4:28 Toby Keith - Should've Been A Cowboy (Live on SoundStage - OFFICIAL) 4:13 Jason Aldean – Should've Been A Cowboy [Toby Keith Tribute] (Live from the 59th ACM Awards) 3:45 Toby Keith - Should've Been A Cowboy (1994)(Music City Tonight 720p) 3:27 Should've Been a Cowboy - Toby Keith 8:26 Toby Keith Sings American Soldier with 10 Year Old Fan at Blossom Music Center 6:03 \"Should've Been a Cowboy\" - Kitchen Dwellers ft. Daniel Donato 3:52 Toby Keith Live Performance of \"Should've Been A Cowboy\". 2019 7:37 Toby Keith performs \" Sould've Been a Cowboy\" & \"Who's Your Daddy\" live in concert 2017 HD 1080p 4:47 Shoulda Been A Cowboy - Dave & Sheldo - Toilet Paper Shortage Tour 12:10 Toby Keith Opens Up About His Battle With Cancer And Decades Long Career 4:49 mgk & Jelly Roll - Lonely Road (Official Music Video) 4:48 Toby Keith - Who's That Man (1995)(Music City Tonight 720p) 6:34 A Patriotic Thanksgiving with Toby Keith and Cowboys 1:17 The Story Behind \"Should've Been A Cowboy\" 3:58 Malvasio - Coulda Been a Cowboy - Original Song 3:23 Toby Keith - Should've Been A Cowbo (Lyric) 3:21 Carrie Underwood – Should’ve Been A Cowboy (Live From The Opry) 4:03 Down On The Farm - Should've Been A Cowboy (Toby Keith Cover) 4:10 Jason Aldean – “Should've Been A Cowboy\" Toby Keith Tribute (Live from the 59th ACM Awards) 3:25 1992 Dallas Cowboys \"Shoulda Been A Cowboy\" by Toby Keith 1:03 Toby Keith \"I Should Have Been a Cowboy\" (Dallas Cowboys Version)