Who's Been the Sturgill Simpson of Every Grammys This Millennium?

Reto Sterchi
Sturgill Simpson

Looking back at the outlier artists who have represented the old guard at every 21st-century Grammys.

The Grammys have always loved to keep things interesting -- or boring, depending on your perspective — in their album of the year category. It seems like every year, amidst the normal roster of commercial heavy-hitters and critical favorites, there's one artist whose presence, due to some combination of relative commercial obscurity, marginal mainstream relevance and general lack of non-Grammy-related buzz, feels at least somewhat inexplicable.

This year, it's absurdly easy to spot the One Not Like the Others. The 2017 album of the year field consists of four megastars, whose albums had the four biggest debut sales weeks of the accompanying period... and Sturgill Simspon, an acclaimed singer-songwriter who achieved impressive, if modest, chart success with the breakout album A Sailor's Guide to Earth. Has it been so obvious in other ceremonies this century? And how many times have these albums actually won? Let's take a look back and see.

2000: Diana Krall, When I Look in Your Eyes

The first album of the year race of the new millennium was appropriately filled with TRL-approved mainstream pop -- TLC's Fanmail, Backstreet Boys' Millennium and a bizarrely resurgent Santana's Supernatural -- but also found room for 35-year-old standards singer Diana Krall, whose fifth album When I Look in Your Eyes became the first jazz album in 25 years to be recognized in the Grammys' biggest category.

Did It Win? No. With their unlikely mix of oldster cred and youngster relevance, there was no stopping Santana at the turn of the century.

2001: Steely Dan, Two Against Nature

Throw in Paul Simon's You're the One here too -- two comeback albums from '70s fixtures who had long drifted from pop's center but who resurfaced to general acclaim, if not Supernatural-like commercial hysteria.

Did It Win? Oh yes. In one of the most infamous upsets in Grammy history, Walter Becker and Donald Fagen took the stage instead of Eminem or Radiohead, delivering an exceedingly unsatisfying acceptance speech that's been understandably scrubbed from YouTube.

2002: Various Artists, O Brother, Where Art Thou? soundtrack

Really, it'd be easier to isolate the non-Sturgill from 2002: U2 and Bob Dylan were both recognized for late-period albums, while India.Arie parlayed her one year of major mainstream visibility into an unlikely AOTY nod. But the ultimate in outliers must remain the Americana recordings on the T Bone Burnett-produced soundtrack to the Coen brothers' hit 2001 movie O Brother, Where Art Thou?, one of the least predictable commercial blockbusters of the entire rock era.

Did It Win? Yep, beating OutKast's Stankonia, which must seem particularly perplexing to music fans under the age of 25.

2003: Norah Jones, Come Away With Me

Neither Norah nor O Brother are perfect examples of the Sturgill phenomenon, since both were major (if impossibly fluky) commercial successes at the time, but both were otherwise so far outside the mainstream that they still feel like anomalies in their respective years -- certainly more so than Nelly, Bruce Springsteen, Eminem and The Dixie Chicks, 2003's other four nominees.

Did It Win?: Not only that, it swept the four major categories.

2004: The White Stripes, Elephant

Again, not an ideal example, as Elephant was a blockbuster album for The White Stripes, and lead single "Seven Nation Army" has endured as one of the century's few obvious future classic-rock standards. But 2004 was a rare year of fairly consistent currentness among the album of the year nominees, also including OutKast, Evanescence, Justin Timberlake and Missy Elliott.

Did It Win?: No, OutKast's double-album Speakerboxxx/The Love Below -- which secretly might've been an even more backward-looking album than Elephant, at least for Andre 3000's latter half -- took it instead.

2005: Ray Charles, Genius Loves Company

This was another year of impressive modernity for the Grammys, recognizing chart-busting albums by Green Day, Alicia Keys, Usher and (for the first time) Kanye West. The one exception: Ray Charles' collaborations album Genius Loves Company, released months after the soul legend's death (and months before his Oscar-winning biopic, Ray).

Did It Win?: Natch -- the album was powerful enough as Grammy bait before the Hall of Famer's passing. After that, it was a total no-brainer.

2006: Paul McCartney, Chaos and Creation in the Backyard

Despite being one of the most influential and successful artists in the history of popular music, Paul McCartney stuck around long enough to find himself in Sturgill territory at two separate Grammys: First in 1998, when his Flaming Pie showed down with Bob Dylan and Radiohead for album of the year, then in 2006, when his Chaos and Creation in the Backyard shared the category with Mariah Carey, Gwen Stefani and (again) Kanye.

Did It Win? No. As in '98, when Dylan took home top honors, Macca again lost out to a fellow past-his-commercial-prime competitor, with U2 winning for How to Dismantle an Atomic Bomb.

2007: Red Hot Chili Peppers, Stadium Arcadium

Only RHCP by process of elimination: They were still just as mainstream as Gnarls Barkley, Justin Timberlake, John Mayer or The Dixie Chicks in the mid-'00s, but having been around for a couple of decades, they were already carrying a faint whiff of veteran tokenism.

Did It Win?: Thankfully not, as The Dixie Chicks received the album of the year Grammy as a sort of consolation prize for their public iconoclasm costing them a truly unfair percentage of their massive fanbase.

2008: Herbie Hancock, River: The Joni Letters

Vince Gill's These Days also fell pretty far outside the zeitgeist in 2008, and Foo Fighters' Echoes, Silence, Patience & Grace was trending in that direction itself. But neither compares to Herbie Hancock's album of Joni jazz covers, one of the least mainstream albums ever nominated for the award, and one that -- unlike Norah Jones or O Brother -- had yet to experience any degree of notable commercial success before the awards show.

Did It Win?: You know it. In a victory that appeared to surprise no one so much as Hancock himself, River emerged triumphant over Kanye's Graduation (0-3!) and Amy Winehouse's Back to Black, setting a new standard for unapologetic Grammy retro-vision in the process.

2009: Robert Plant & Alison Krauss, Raising Sand

Another year of sore-thumb-obvious Sturgillness: Radiohead, Lil Wayne and Coldplay released three of the year's most impactful albums, and even Ne-Yo was still at his top 40 commercial peak. However, with the possible exception of Radiohead, none of those artists had the grandfathered-in prestige of Robert Plant and Alison Krauss' folky one-off collaboration.

Did It Win?: T Bone Burnett strikes again. Raising Sand escaped with the win here, a back-to-back with River that confirmed that the Grammys were more comically out of touch than ever.

2010: Dave Matthews Band, Big Whiskey and the GrooGrux King

The changing of the pop guard at the end of the '00s was well-represented in the '10 album of the year nominees, with The Black Eyed Peas, Lady Gaga and Taylor Swift -- arguably the three biggest artists in pop (except of course for Beyoncé, who merely handed the baton off to her own alternate identity Sasha Fierce) -- being recognized. But that left room for one more potential grizzled ol' fly in the ointment, in the form of Dave Matthews Band's first album in five years, Big Whiskey and the GrooGrux King. It couldn't really happen three years in a row... could it?

Did It Win?: Nope: Taylor and Beyoncé saved the Grammys from themselves, with Swift taking home album of the year and Bey sweeping up nearly everything else, injecting much-needed new blood into the show's canon.

2011: The Arcade Fire, The Suburbs

Megapop continued to reign at the '11 ceremonies, with Gaga (receiving her second AOTY nomination in a row) rubbing shoulders with Katy Perry and a top 40-revived Eminem -- even Lady Antebellum crossed over in a major way with the title track to their similarly nominated Need You Now. That left The Arcade Fire, without even a Billboard Hot 100 hit to their credit, as the outlier, for their Springsteenian dead-end-town opus The Suburbs.

Did It Win?: Yes, but despite the confusion among the young-teen set, this one wasn't quite as embarrassing as some past victors -- The Suburbs was the year's most acclaimed rock album, and a chart-topper in its own right.

2012: The Foo Fighters, Wasting Light

The Foos were undoubtedly still quite popular by the time of their second album of the year Grammy nomination, but by that point the band was more famous for frontman Dave Grohl's grandstanding as rock's last True Believer than he was for any song he had written in the past decade. In a class with emerging pop icons Lady Gaga (third time's the charm?), Bruno Mars, Rihanna and Adele, it was clear that Foo Fighters were the closest to fossilization.

Did It Win: No, and Adele may very well never lose at the Grammys again.

2013: Jack White, Blunderbuss

Likely to go down as the last Grammy year for some time where the rock album of the year nominees outnumber the non-rock, at least if you count fun. or Mumford & Sons under the rock umbrella. Both of those acts were contenders for top honors in '13, as were nouveau classic-rockers The Black Keys, and while oldster-in-spirit Jack White was the most superficially Sturgill-y of the crop, fifth nominee Frank Ocean was perhaps the year's true anomaly.

Did It Win?: No, and neither did Ocean -- Mumford & Sons, who just three years ago were somehow about as big a commercial powerhouse as existed in popular music, took it in a walk.

2014: Sara Bareilles, The Blessed Unrest

Bareilles was only a half-decade removed from her breakout when The Blessed Unrest scored an album of the year nomination, but her recognition still felt bizarrely behind the times -- especially as compared to fellow nominees like Kendrick Lamar, Macklemore and Ryan Lewis, and even Taylor Swift, whose pop arrival technically predated Bareilles'.

Did It Win?: No -- she was defeated by Daft Punk, an act who'd already been around for ages, but thanks to the cultural saturation of "Get Lucky" and EDM's long-overdue rise to power over the few years prior, the robots felt like the most relevant act of the bunch.

2015: Beck, Morning Phase

We all remember this one -- pop players Ed Sheeran, Pharrell, Sam Smith and Beyoncé, the latter having turned the entire music industry upside-down with her nominated self-titled album, squared off in one of the most stacked top 40 showdowns in recent Grammys history. But a fifth guest was invited to the party in Beck Hansen, the alt-rock trailblazer who'd unfairly lost a couple albums of the year of his own to Celine Dion and Steely Dan decades earlier, but who by the time of 2014's dolorous Morning Phase was much more the face of the rock establishment of yesteryear.

Did It Win?: Certainly did, and even Beck knew it was gonna be trouble, practically begging a stage-threatening Kanye not to let him finish.

2016: Alabama Shakes, Sound & Color

And that brings us to last year, where the NPR-approved but otherwise radio-marginalized Alabama Shakes (and to only a slightly lesser extent, country vet Chris Stapleton) mixed it up with Kendrick Lamar, Taylor Swift and The Weeknd in our most recent Old World vs. New World Grammys showdown.

Did It Win?: Nah, you might remember Taylor up there for 1989, subtweeting Kanye West for his fame-credit hogging, an event that certainly led to its fair share of fallout later in the year. Brittany Howard and the Shakes did give a kick-ass performance, though, and even if the moment has now passed for Sturgill to pull a Beck-sized upset himself, getting the chance to deliver one of those himself will undoubtedly still make for a pretty solid night's work.

2017 Grammys