If you look up controversial Grammy Album of the Year winners, one of the most common you’ll find referenced is Steely Dan’s “Two Against Nature.” The band’s eighth album proved to resonate with Grammy voters, taking home multiple awards including the top prize. But many weren’t as enthusiastic as the Recording Academy, arguing that there were better and more impactful records in the lineup. So let’s take a look at the win, how it happened, and why it might not have been that surprising at all.

Steely Dan weren’t strangers to the Grammys prior to their 2001 win. The group had gotten six noms from 1975 to 1982, including Album of the Year nominations for “Aja” and “Gaucho.” However, the group never actually won a Grammy, and went into a two decade hiatus after “Gaucho.” So when news came that the group was coming back after 20 years,...