As far as being the best song on Toby Keith, a couple come close like Wish I Didn’t Know Now, Valentine, and He Ain’t Worth Missing but all fall short of the first track Should’ve Been a Cowboy. The song was written after a night baring where Keith’s highway patrol friend asked a girl to dance where she said she didn't dance, but then later hit the dance floor with a young cowboy to which one of his friends said “You should’ve been a cowboy”. The lyrics referencing Western culture and characters drive home the story it tries to sell, and that it does amazingly. The song’s vocals and composition help the single propel its way to the top of the album. The song’s greatness can be seen by its success as a single going 3x platinum and being the most played song on country radio in the 90’s. The song solidifies itself as one of the best released for an amazing era.

As hard as finding the best song on Toby Keith, finding the worst was just as hard since the album has no shortage of amazing songs. Compared to the best one seems to stagger back from the others, that song being Mama Come Quick, the 9th track on the album. The song is written in a retrospective tone going through life as a kid falling off his bike, falling in love, and getting heartbroken. Then the song describes how much a mother's love can help heal through all of those situations and how much he still depends on her. While sentimental, the song often seems repetitive with the constant repetition of the titular phrase used in the title. The song's vocals and backing track are good and help lift up the track to still being a good song but it seems to fall short when compared to the rest of the album and its mastery of the early 1990s country sound Keith helped to make famous.