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.