I can remember the palpable air of anticipation we felt at the end of the 90s, how impossibly important it sounded when people on TV chattered on and on about the coming millennium. Automatic gravitas: we talked about 1999 in terms of how we would party, but gave a sort of mystical deference to the following year. It was always the starchy, formal reference—“The Year Two-Thousand”—or that epithet, “The New Millennium.” Easy to forget, but in their pomp, those terms carried the swagger only the future (and its ever-present promises) could ever walk with.

Despite ourselves, there was a tangible sense that big changes were in the works if we could only make it there. In 1999, even Mos Def felt compelled to express that most basic urge to stay alive in terms of wanting to make it across the line: four MCs murdered in the last four years / I ain’t trying to be the fifth, the Millennium is here. On other fronts, all the Doomsday Preppers had whipped themselves into the Y2K frenzy, and one or two of them could always be seen frothing at the mouth in your neighborhood grocery store, hunched over a shopping cart full of dented cans. In March of 1999, The Matrix premiered, and we were all transfixed, certain that what we had seen was fiction, and that it was oh so relevant because somewhere, at that very moment, someone was designing a race of machines to rule us all (just as you ought to be sure that some disappointed weirdo is doing it now). Shit was thick: End Times wasn’t (and probably isn’t) an entirely ridiculous suggestion. And up from that weird trough of chaos came what?

Manu Chao’s wild, sad, rich, and occasionally cacophonic second album Próxima Estación: Esperanza emerged from a world obsessed with its own end (under the strong assumption at the hands of the machines it created). Esperanza blew up all across Europe in 2000—and finally hit the US in 2001, where it achieved moderate success, which, if you think about it, is astounding in and of itself. Where on earth do we place Spanish-born/French-raised, hardcore unblinking and unapologetic left-of-leftist badass Manu Chao and his second record in the context of the history of the New World, or even just America—let alone within the context of the Anglo-heavy Rolling Stone 500?

Best guesses:

One (thumb)

What do you reckon? I say it’s the case that a jury room full of old-ass founding fathers would’ve loved Pet Sounds and Sgt. Pepper’s Lonely Hearts Club, ate their hearts out, even; that they would have been happy to give either album the Number One Spot on their own Exhaustive Magnum Opus List of great albums; they would’ve gasped and squealed with delight the first time they heard the intro to “Wouldn’t It Be Nice,” or saw a bunch of British people acting like jackasses because their day jobs afforded such creative license in a time of Cold War and leisure. Imagine it: me, you, Brian Wilson, John & Yoko, and Benjamin Franklin, tipsy, tripping maybe, and square-center of the petting zoo, desperately trying to cobble together a plan of where to go next.

Two (index and middle)

This much I’m sure: all them frail-old-dead-presidents’ eyes would have been glittered over with proud grandpapa tears (no doubt to be dabbed at with a lacy kerchief and a stiff upper lip air of dignity); and then in self-consciousness, they’d sniff and blow their noses, and they’d chuckle and congratulate each other: haw-haw, what a country we have made. Benjamin Franklin would pour everyone another glass of Madeira and they’d sing God knows what—“He’s a Jolly Good Fellow,” and other gentleman songs. They’d marvel and say, Rock ‘n’ Roll: what a gorgeous thing we have wrought.

Three (thumb, index, middle)

The founding fathers are, of course, the epitome of the stone gathering moss. Jefferson’s big-ass-rock-at-Monticello gathered enough moss to leave his kin with six-figure debt in an age of five-figure personal finance (the President’s salary was $25,000 at that time—still more than the average line cook or barista with a law degree makes now). Thomas Jefferson, with his deep personal failures of ethics and finance, still did a lot of productive rabble-rousing at least. He might well be the best of the bunch in that regard—and the coexisting truth is that in some very important human ways, he sets a very low bar, indeed.

Four (thumb, index, middle, ringless-ring)

Now this is important to point out as well: them salty old horsemeat sandwiches beat the British and gave us a platform on which we had room to change things and build a badass country. But, each in his own way was as much a cruel, cowardly, lucky piece of shit as any un-human critter has ever walked and breathed. That’s a fact.

Five (thumb, index, middle, ringless-ring, pinky)

Leaving behind the long-term past for only a moment, you might know that they call Manu Chao “El Tarzan de Catalunya,” and that he often goes about his business without a shirt. See it as your weird, Everybody Loves Raymond-watching uncle saw it in the 90s: Woody Guthrie speaking French, Arabic, Portuguese, Italian, and, most often, Spanish, travelling extensively in Latin America and the Caribbean, with no interest in mineral or oil rights. A dictator persecuted his family. He openly and fully supports the Zapatistas, and is rumored by the Internet to be friends with Gogol Bordello. Utter chaos.

And so Próxima Estación: Esperanza lands at #474 on the list, no one willing to commit to anything other than the importance that the album be allowed to exist while everyone waxes nostalgic about the first time they heard The Who. Problematically, it (arguably) isn’t even Manu Chao’s best work.

Próxima Estación: Esperanza might not have the grit of Chao’s first album, Clandestino, but it’s going to stay iconic for a reason. If Pet Sounds sits fat and puffy at the top of the pile with Sgt. Pepper’s Lonely Hearts Club Band, we can forgive Esperanza’s tendency to play around so many sounds, because it takes a travelling Spaniard to tells us what to make of our neighbors, of ourselves, of the new world order and the New World. It takes the Merry Blues to sound like the Americas, and it takes an unspeakable hubris to think a magazine list curated by accountants could ever do justice to Manu Chao or “his wild-ass greatness.”

And to be sure: these days, there’s lots of HOPE ‘08 bumper stickers, faded from winter salt and rain. The legacy of drone-killings and an unchecked surveillance state are things we’re going to have to grapple with for a long time yet. Mexico and Brazil, even with unspeakable oil wealth, still falter. Chile, post-Pinochet, has emerged as one of the happiest, least-corrupt places on the planet. Argentina won’t take the national jet out of the country on account of bad debts and fear of repossession by their foreign creditors. Everywhere you look, the map of the new world outpaces our ability to wrap our mind around it quick enough to adjust.

We’re trying desperately to cobble together a coherent vision, a plan of what to do next. There’s no precedent, no blueprint for this. Manu Chao, however, still pops up every now and again to play a show in front of the Maricopa County Jail in Arizona, to sing “Clandestino” acoustic and majestic. He’s got grit, and he’s got great-ass wildness; he’s got the deep sadness, and still sleeps on people’s floors. He’s goofy, righteous, and spectacularly cool. He is, in the broadest, grandest sense, what that every American kid in the 90s wanted so badly to become as we tried to navigate the sense of danger and big deeds the millennium would bring. Go on: put the poster on your wall. It says, next station: hope. We need that shit bad here in the future.

—Aaron Fallon