In recent years, one Grammy contest that has been misunderstood is Album of the Year in 2000, when '70s jam-band Steely Dan's "Two Against Nature" upset the heavily favored and extremely controversial Eminem for "The Marshall Mathers LP." Their victory is usually thought of as simply the Recording Academy rewarding a veteran performer, as they are wont to do in that category (Santana in 1999, Ray Charles in 2004, Herbie Hancock in 2007). But a closer look at the circumstances surrounding the album show there was more to it than that.
It is important to understand the history of the band. Steely Dan, the brain child of vocalist/keyboardist Donald Fagen and guitarist Walter Becker, debuted in 1972 with the album "Can't Buy a Thrill." The album was an instant success, with a conventional sound for a pop/rock album in the early 1970’s. Subsequent efforts didn’t always fare as well commercially, but did do well critically, and further cemented their defining sound. Their loose blend of pop, rock, and jazz culminated on their albums "The Royal Scam" (1976), "Aja" (1977) and "Gaucho" (1980); the latter two received Grammy nods for Album of the Year.
But after the release of "Gaucho," with both Fagen and Becker dealing with personal, health, and substance abuse problems, the duo went on an extended hiatus. They rekindled their friendship several years later and in the mid-1990s began touring again. Then in February 2000, they released their first album of new material in 20 years: "Two Against Nature," which was not only a critical success (it scores 77 on Metacritic) but a hit commercially as well: it debuted at number-six on the Billboard 200 and was certified gold (500,000 copies sold) one month later.
What was most astonishing about the record was the fact that the band had done something thought to be almost impossible: they sounded like they had picked up right where they left off in terms of their style, and the 20-year hiatus didn't seem to factor into how the album sounded at all.
It's also important to remember that the music industry as a whole was going through a crisis when these Grammys were decided. The issue of peer-to-peer file sharing and the high-profile court cases against Napster were throwing the music industry into conflict over what the future of the business would be. Some feared that the very idea of an album would become obsolete, with people downloading only the songs they wanted.
Steely Dan, however, was known as an album-oriented band. While they did release singles, it was their musical choices in shaping their albums as a whole that made them successful. This turned the support for "Two Against Nature" into a powerful message: by voting for it as Album of the Year, the powers that be in the music industry were able to say that they were not going to let companies like Napster destroy this traditional form of music making.
When you also consider that the group had never won a single Grammy before, Eminem's controversies and Grammy disses on his album, and the fact that nominated alternative acts Radiohead and Beck were probably a bit beyond the grasp of older members of the Recording Academy, and you get a better idea of why "Two Against Nature" was their choice as Album of the Year for 2000.