Why Cousin Dupree By Steely Dan Was Their Most Bizarre Grammy-Winning Song

March 21, 2025

In the heart of the 1970s, when rock music was blossoming like never before, a band called Steely Dan was capturing the attention of listeners with their unique sound. Led by the brilliant duo of Donald Fagen and Walter Becker, they combined jazz, rock, and pop in ways that were both innovative and intriguing. Their music was anything but ordinary; it often told strange stories that left listeners both puzzled and fascinated. Among their many recordings, one song stood out as particularly bizarre: “Cousin Dupree.” This tune would eventually win a Grammy, but not without sparking a whirlwind of opinions and reactions.

“Cousin Dupree” is an odd story about a man in love with his cousin, filled with quirky lyrics and a catchy groove. When it was released, people scratched their heads, unsure whether to laugh or cringe. Fagen and Becker were known for their clever yet unconventional storytelling, but this song pushed the boundaries of what was acceptable in popular music. Some fans loved the playful absurdity of it, while others were taken aback, feeling that it crossed a line. Yet, the song became a symbol of the duo’s fearless creativity, showing that they were not afraid to tackle themes that others might shy away from.

Winning the Grammy Award for Best Pop Performance by a Duo or Group in 2001 was a defining moment for Steely Dan, but it was both a blessing and a challenge. While they celebrated their victory, they also recognized the mixed reactions from critics and fans alike. Some said that winning for “Cousin Dupree” was a sign of the music industry’s unpredictable nature, a reminder that what might seem bizarre could also be celebrated. Instead of letting the criticism get to them, Fagen and Becker embraced the recognition, using it as fuel for their passion for music. They understood that not everyone would appreciate their art, and that was okay.

As they reflected on their journey, Steely Dan realized that their willingness to take risks set them apart in a crowded industry. Their love for creating music that was authentic to them, even if it didn’t always follow the traditional path, inspired countless other artists. They became a beacon for musicians everywhere, showing that it was possible to chase your vision, regardless of whether others understood it. This lesson in resilience and dedication resonated deeply, reinforcing the idea that art should challenge norms and provoke thought.

In the years following their Grammy win, “Cousin Dupree” remained a staple in Steely Dan’s repertoire, a beloved song in concert that illustrated their growth and evolution as artists. The quirky, tongue-in-cheek tale took on a life of its own, often eliciting laughter and sing-alongs from audiences. The duo continued to create music that pushed boundaries, each new album building on their legacy of creative fearlessness.

Looking back, “Cousin Dupree” exemplified everything Steely Dan stood for: boldness, creativity, and the power of storytelling through music. They proved that even the most bizarre ideas could resonate with people and encourage conversations about love, family, and the complexities of relationships. Their journey taught fans that music is not just about pleasing everyone; it’s about being true to oneself and sharing experiences that may seem strange at first but hold a deeper truth within. And that, in itself, is the beauty of art.