The battle for the 2008 Album of the Year Grammy was a classic showdown between two commercial and critical heavyweights.

Kanye West’s acclaimed Graduation album had sold just under 1m copies in its first week. Featuring the Daft-Punk-sampling single “Stronger,” it was his third consecutive album to be nominated for AOTY, and West had already picked up 4 Grammys that evening, including Best Rap Album.

Meanwhile, Amy Winehouse was enjoying an even more impressive night, even if she was unable to attend the L.A. ceremony due to work-visa issues stemming from a recent drug rehabilitation stint. Beamed into living rooms from Riverside Studios in London, Winehouse delivered a mesmerizing performance of “You Know I’m No Good” and “Rehab” from her breakthrough album Back to Black. “Rehab” would win both Record and Song of the Year, and Winehouse had already earned the Best New Artist trophy. She was a perfect 5 for 5 heading into the final award of the evening.

At the dawn of the century, however, Grammy voters were a largely middlebrow and mercurial bunch, even more so than today. Since 2000, they’d lavished a bluegrass soundtrack, O Brother, Where Art Thou?,” with five Grammys, including AOTY; made jazz-pop singer Norah Jones a household name; and determined that Ray Charles’ posthumously released duets album, Genius Loves Company, was more deserving than Usher’s Confessions and West’s The College Dropout, blockbusters both.

So when presenter Quincy Jones announced, with equal parts surprise and elation, that the Album of the Year was Herbie Hancock’s River: The Joni Letters, Hancock’s look of complete shock as he bounded up to the stage was matched by many at Staples Center, a fair percentage of whom had never heard, or even heard of, the album in question.

Jazz great Hancock had joined with his fellow Miles Davis alums Wayne Shorter and Dave Holland to pay tribute to the music of Joni Mitchell, certainly no stranger to jazz herself. River, featuring vocal performances from Jones, Tina Turner and Leonard Cohen, performed admirably for a jazz album, peaking at #118 on the Top 200.

Following the Grammy win, the album jumped all the way to #5.

“It’s been 43 years since a jazz artist got the Album of the Year award,” announced Hancock in his acceptance speech, casting back to 1965, when Stan Getz and João Gilberto won for Getz/Gilberto. “And I’d like to thank the Academy for breaking the mold this time.”

Later in the press room, Vince Gill, who was also nominated for AOTY (the Foo Fighters were the fifth nominee) was asked about the upset victory, one of the more remarkable in Grammy history. “Hancock,” he said, “hands down, is a better musician than all of us here put together.