Inspired by Oklahoma Today‘s September issue focusing solely on country music, we’ll be counting down the Top 100 Oklahoma Country Songs over the next several weeks.
Every weekday, we will unveil another five songs that helped shape the way Oklahoma country music is heard by the outside world.
20. Toby Keith – “Should’ve Been a Cowboy” (1993)
On his debut single, Toby Keith wrote and sang a wistful tune about living in a different era with this No.1 hit for 1993.
Name dropping singing cowboys like fellow Okie Gene Autry and Roy Rogers, Keith rode “Should’ve Been a Cowboy” until it became the most played country song of the 1990s.