With his surprise win for best album Sunday night, Hancock joined a rich tradition of infamous Grammy winners that immediately caused audience members to contort their faces in curiosity and disbelief.
The 67-year-old jazz pianist wasn't only the surprise winner, he was a surprise nominee. When the Grammy nominations were announced in December, a blogger for Spin Magazine wrote: "This award is meant to expand beyond the reach of pop and rock, but Herbie Hancock? Really?"
As it turns out: Yes, really.
Hancock's Joni Mitchell tribute album, "River: The Joni Letters," was neither a financial success (it has sold a paltry 56,000 copies according to Nielsen SoundScan) nor a particular critical darling.
Amy Winehouse, on the other hand, was one of the most common selections among critics' top-ten lists. Though she won for best record ("Rehab"), best song ("Rehab," again) and best new artist, Winehouse failed to sweep.
If Grammy voters had wanted to take a more populist approach, Kanye West was the favorite. The Chicago rapper's "Graduation" was one of the year's biggest sellers. He still collected four awards, but again left the Grammys disappointed in losing best album.
Instead, Hancock came out of left field to win the night's big award. Even he was shocked, rating his surprise as "immeasurable."
Hancock's upset immediately recalled past Grammy wins that have roundly been mocked. In 2001, Steely Dan (then long past its prime) won best album over Eminem, Radiohead and Beck.
The most oft-cited example of the Grammys being out-of-touch is Jethro Tull (a classic rock band that made their biggest flute-accompanied impression in the `70s) winning for best hard rock or metal performance in 1989, while Metallica waited in the wings.
That still doesn't include the dozens if not hundreds of decisions by Grammy voters that in hindsight look downright foolish. In 1985, for instance, Lionel Richie's "Can't Slow Down" beat two albums so legendary that their authors need no mention: "Purple Rain" and "Born in the USA."
And then there's Milli Vanilli winning best new artist in 1990, which the Grammys and everyone else would prefer to simply forget.
(The award was withdrawn four days after the ceremony.) Hancock, undeniably, is no Milli Vanilli. His skills are undiminished with age and he remains one of few living jazz greats.
But he's also arguably long past his heyday, which spanned his early work in Miles Davis' band in the `60s and his revolutionary synthesizer-heavy fusion work in the `70s.
On Monday, following his Grammy win, fans were rushing to buy "River: The Joni Letters," which ranked as the no. 1 album on Amazon.com and was fast climbing the most-purchased albums list on iTunes. New listeners, though, would likely be better served reaching for Hancock's "Maiden Voyage," released in 1965, or his 1973 classic "Head Hunters."
The appeal of "River: The Joni Letters" is in its more overt pop structures. As covers of Mitchell's songs, the album is also full of luminary guests, including Norah Jones, Tina Turner, Corinne Bailey Rae and Mitchell herself.
In his acceptance speech, Hancock may have characterized his win as the first for a jazz album in over 40 years, but it's not a typical jazz album. Given its material and guests, "River" may have more in common with, say, Ray Charles' "Genius Loves Company," the duet-laden best album winner of 2005.
As an institution, the Grammys - which was celebrating its 50th anniversary Sunday - have never been renown for progressivism or even common sense. They've often struck devoted music fans as irrelevant; it's not difficult to take shots at any grand award ceremony that has lavished honors on Alvin and the Chipmunks and Christopher Cross.
But as the 100-plus categories attest, music is an incredibly expansive and subjective art form.
In recent years, the Grammys have tried to shake off any stodginess and could point to best albums winners like OutKast, U2, Lauryn Hill and the sensational "O Brother, Where Art Thou?"
soundtrack as proof.
Recording academy president Neil Portnow defended Hancock's win backstage on Sunday: "I don't think sales has anything to do with what the academy decides in awarding albums or records. It's about excellence in music," he said. "It was a very respectable choice."
