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When Wilco won the Best Historical Album Grammy

The win for the deluxe remastered version of Wilco’s ‘Yankee Hotel Foxtrot’ has turned the spotlight on a 20-year-old album acclaimed as a masterpiece

‘Yankee Hotel Foxtrot’ really defines the Wilco sound.
‘Yankee Hotel Foxtrot’ really defines the Wilco sound.

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For more than four decades, the Grammy Award for Best Historical Album has usually been given to albums that achieve excellence in the audio restoration of relatively old recordings. Awardees have included jazz legends such as Lester Young, Billie Holiday and Thelonious Monk, classical music conductors such as Arturo Toscanini, early country music superstars such as Hank Williams, folk greats such as Woody Guthrie and select volumes of Bob Dylan’s Bootleg series—all mostly relatively old recordings. This year, the award, a bit surprisingly, went to an album titled Yankee Hotel Foxtrot by a very contemporary band, Wilco.

First released in 2001, Yankee Hotel Foxtrot was reissued last year in a deluxe remastered version that included unreleased tracks. The Grammy was awarded to the deluxe reissue. The adjective “historical” might sound misplaced when it is used to describe an album that is just 20 years old but the album, Chicago-based alternative rock band Wilco’s fourth full-length, is a work of seminal proportions. When it came out—barely a week after the 9/11 attacks rocked the US and the world—it was instantly and almost universally acclaimed by critics as a masterpiece, taking American rock music in a whole new and complex direction.

Yet, there was a chance that the album might never have been released commercially. The 2001 release was actually a free streaming release by the band on its website after their record label, Reprise (owned by Warner Bros), refused to release it because it thought it wouldn’t have wide appeal. The rights were passed back to Wilco. The album got immediate critical approval and a cult following. Then, ironically, another label from the Warner stable, Nonesuch, signed the band and launched the album in 2002.

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Wilco was founded by its frontman Jeff Tweedy after the demise of his earlier band, Uncle Tupelo, one of the first alternative country music bands. Alt country is a very loosely defined genre but often it has bands inducting the guitar-driven elements of punk rock into traditional country music. At Uncle Tupelo, Tweedy and co-founder Jay Farrar probably did it the best. Their first album, 1990’s No Depression, became a synonym for the genre.

Uncle Tupelo disbanded in 1994. Tweedy, mainly a singer and songwriter, teamed up with multi-instrumentalist Jay Bennett to launch Wilco. Their first album, A.M. (1995), sounded like an extension of UncleTupelo—alternative country. Their second, Being There (1996), was an experimental foray into rock, with songs that had noisy interludes and brooding lyrics. It was clear that they were taking steps towards something that was still in a formative stage (check out how the album’s opening track, Misunderstood, unfolds).

Then came Summerteeth (1999). The chemistry between Bennett, an especially talented keyboardist, and Tweedy had evolved into a signature sound that could be at once tender and emotionally endearing but also unpredictably off-kilter and trippy (listen to I’m Always In Love on that album).

Then came Yankee Hotel Foxtrot, which really defines the Wilco sound. It is not difficult to see why the band’s original label, Reprise, passed on the album. The suits just didn’t get it. When you hear the first track on Yankee Hotel, I Am Trying To Break Your Heart, with a bit of feedback noise and a distant snare drum riff that seems hesitant and unsure, followed by muted keyboard notes, you may wonder what it’s leading to. Then Tweedy’s moody vocals join in: I am an American aquarium drinker/ I assassin down the avenue/ I’m hiding out in the big city blinking/ What was I thinking when I let go of you? Is it a break-up song? Is it about addiction? Is it about longing? Is it about sex?

That is the kind of mood Wilco songs can often get you into—by way of both lyrics and music. But then, the same album has the peppy (and probably “poppiest” track on Yankee Hotel Foxtrot) Heavy Metal Drummer, an upbeat song that can quickly become an earworm as Tweedy sings: Oh, I sincerely miss those heavy metal bands/ I used to go see on the landing in the summer/ She fell in love with the drummer/ She fell in love with the drummer/ She fell in love…

Since its release, Yankee Hotel Foxtrot hasn’t sold millions of copies. According to Recording Industry Association of America statistics, it has sold under 600,000 copies. But that is more than enough to have made it an iconic cult album. It also turned Wilco into one of America’s most significantly influential bands, one some critics have described as America’s Radiohead. Later bands such as The War of Drugs and The National have on various occasions acknowledged Wilco’s influence on them.

Since Yankee Hotel, Wilco have released eight more studio albums (Bennett is not on them; he left after disagreements with Tweedy in 2002 and then, sadly, died). Their latest, 2022’s Cruel Country, an unexpected revisiting of the early alternative country explorations that Tweedy had (sort of) pioneered in Uncle Tupelo, shows that Wilco continue to surprise.

Those who like Wilco should watch the documentary I Am Trying To Break Your Heart: A Film About Wilco (2002). It is insight into how focused Wilco are on their music, shorn of the unnecessary trappings and image-building that many other over-produced contemporary bands resort to.

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