Toby Keith’s “Cowboy” Comes Back Around

After paying his dues in the Oklahoma bars and clubs, Toby Keith galloped to the top of the country chart in 1993 with “Should’ve Been a Cowboy.” In his very first video, the young singer wins over a dance hall with his magnetic smile — and he even gets the girl after displaying some gunfighter swagger. Looking back, Keith shouldn’t regret his non-cowboy career path because he’s now one of country music’s most reliable stars. Enjoy this classic video.