Introduction
Toby Keith’s debut single, “Should’ve Been A Cowboy,” released in 1993, is a quintessential country anthem that helped launch his career in country music. Written by Keith himself, the song reflects on the nostalgic yearning for a simpler, more adventurous life—one that is rooted in Western cowboy ideals. Its release came as the first single from his self-titled debut album, and it became an instant success, climbing to No. 1 on the Billboard Hot Country Songs chart and staying there for a remarkable four weeks.
The song’s lyrics focus on a man who contemplates his life choices and wishes he had embraced the cowboy lifestyle—complete with wide open spaces, riding horses, and living freely without the constraints of modern life. Keith’s drawl and storytelling style in the song’s verses painted a picture of the American West, filled with longing and romance. The central line, “Should’ve been a cowboy,” became a catchphrase that resonated deeply with fans of country music and those nostalgic for the idea of the Wild West.
The music video for “Should’ve Been A Cowboy” portrays Keith in a Western-themed setting, emphasizing the cowboy imagery and incorporating elements of the life he sings about, further cementing the song’s place as a classic in the country genre. The video features Keith performing with his band, dressed in Western gear, and it became iconic for its depiction of country living and rough-and-tumble cowboy themes.
As Toby Keith’s first hit, the song not only launched his career but also introduced his signature blend of country music, humor, and larger-than-life storytelling. It remains a staple in his catalog and a beloved anthem for fans of traditional country music.