2018 marked the 25th anniversary of Toby Keith's debut single "Should've Been a Cowboy" from his debut self-titled album. The album was retitled after Keith's #1 debut single to celebrate the 25th anniversary and rerelease in 2018 with 3 bonus tracks.

Tracklist:

1. Should've Been A Cowboy
2. He Ain't Worth Missing
3. Under The Wall
4. Some Kinda Good Some Kinda Hold On Me
5. Wish I Didn't Know Now
6. Ain't No Thang
7. Valentine
8. A Little Less Talk And A Lot More Action
9. Mama Come Quick
10. Close But No Guitar
11. Tossin' and Turnin'  (25th Anniversary bonus track)
12. I'll Still Call You Baby  (25th Anniversary bonus track)
13. Daddy Mac  (25th Anniversary bonus track)