Introduction
90s Country Icon Toby Keith Reaches Major Career Milestone With Two Songs Decades After Their Release
The landscape of country music has always been defined by its ability to tell stories that resonate across generations. This truth has never been more evident than in the recent, posthumous success of the legendary Toby Keith. Even after his tragic passing in February 2024, the “Big Dog Daddy” continues to break records, reaching a staggering career milestone as two of his most iconic tracks from the 1990s achieve new levels of RIAA certification and streaming dominance decades after their initial release.
Toby Keith burst onto the scene in 1993 with a self-titled debut album that signaled the arrival of a new kind of country star—one who blended traditional honky-tonk grit with a modern, unapologetic swagger. Today, that legacy is being cemented by the renewed surge of hits like “Should’ve Been a Cowboy” and “How Do You Like Me Now?!” These songs have officially crossed major multi-platinum thresholds, proving that Keith’s brand of storytelling is timeless.
“Should’ve Been a Cowboy,” his debut single, recently reached a historic milestone in digital sales and streaming. Originally released in an era of cassette tapes and radio dominance, the song has found a second life on platforms like Spotify and Apple Music, introduced to a younger generation of fans who find comfort in its romanticized view of the American West. It remains the most-played country song of the 1990s on radio, and its new certifications reflect a digital footprint that few artists of his era can match.
Simultaneously, “How Do You Like Me Now?!”—the defiant anthem that redefined Keith’s career in the late 90s—has seen a massive uptick in cultural relevance. The song, which speaks to the triumph of the underdog, has become a rallying cry for fans honoring Keith’s own resilient battle against stomach cancer. This milestone isn’t just about numbers; it represents the enduring emotional connection Keith maintained with his audience.
Industry experts note that this surge is part of a broader “Toby Keith effect.” Following his passing, his entire catalog saw a 300% increase in consumption. However, the fact that his 90s material is leading the charge suggests that the foundation he built early in his career was remarkably solid. These songs were more than just radio hits; they were cultural touchstones that defined an era.
For his family, including his daughter Krystal Keith, these milestones are a bittersweet reminder of his immense influence. “To see him still reaching these heights… it’s such an honor,” a family spokesperson noted. As Toby Keith’s music continues to climb the charts decades later, it serves as a powerful testament to a man who lived and sang with a “steely determination” that will never be forgotten.