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Tyler, the Creator is making it no secret that he wants to win Best Rap Album for his excellent full-length Flower Boy at the 60th Annual Grammy Awards this weekend. Speaking on The Shane Show, the rapper said that “Yes, I think I should win. Something different needs to win.” In other words, someone who isn’t an industry mainstay like fellow nominees JAY-Z, Kendrick Lamar or Migos should nab the trophy (though in all fairness to Tyler, fifth nominee Rapsody would truly be the most ‘different’ win of the bunch).

This got us to thinking – not of the merits of Flower Boy, of which there are many – but of the category of Best Rap Album itself. Considering some of the utterly appalling records that the National Academy of Recording Arts and Sciences has deemed as the ‘album of the year’ (regardless of personal preference, who among us truly thinks that an album of bluegrass standards from a former member of Led Zeppelin was the best piece of recorded music made in 2007/8??), the organization’s selections for the Best Rap Album are often a much more accurate representation of the culture at large’s musical tastes. Lest we forget, hip-hop is now officially the most popular genre in the country, no matter what the industry stalwarts might have us believe.

Since the category’s creation in 1995, 22 albums have taken home the title. Many of these winners are undisputed masterpieces, others are… well, not. And despite it generally being more indicative of our cultural tastes, it sure ain’t perfect. For instance, no woman has ever won this award as a solo artist (Lauryn Hill was honored as one third of Fugees, which is the beginning and end of women winning in this category). And some would be surprised to learn that the artist who has notched the most wins in this category is Eminem, with a whopping six trophies under his belt.

As we eagerly await to see whether Tyler, the Creator will pull an upset at this weekend’s ceremony, we take a look back through the ups, the downs and the who tf knows of the category’s history. Here they are: every winner of the Best Rap Album Grammy ranked from worst to best.

Editor’s Note: the years attached to album titles denote when Grammy was received, not release date.

22. Eminem – ‘Relapse’ (2010)

This is a downright atrocious record. It was received so poorly that we recently learned Eminem scrapped plans for a follow-up, which should surely go down as one of his smarter career moves. Whether it’s baby-talking over a horn section passing gas on “My Mom” or posing as the least-convincing stoner this side of a 10th grade health class video on “Must Be the Ganja,” Eminem is equally off his game on every track. Which is the most cohesive thing this stinker has going for it.

21. Macklemore & Ryan Lewis – ‘The Heist’ (2014)

Is this album so low on this list out of spite? You bet your ass. Consider this – Grammy voters were given a nominee pool that included Kendrick Lamar’s good kid, m.A.A.d. City, Kanye West’s Yeezus, Drake’s Nothing Was the Same and JAY-Z’s Magna Carta Holy Grail and they chose Macklemore and Ryan Lewis’ The Heist. It was a decision seen as so universally egregious that Macklemore famously called Kendrick to apologize for stealing his trophy, as he rightfully should have. Even an album on which JAY-Z stutters the words “Picasso baby” for four minutes straight is more of a tolerable listen than any second of Macklemore’s sickeningly sweet attempts at being fun, cute and creating an LGBT anthem which he has absolutely no right making as a cisgendered, straight, privileged white man.

20. Eminem – ‘The Marshall Mathers LP 2’ (2015)

The Grammys’ bizarre obsession with Eminem reached its zenith by awarding yet another of his seemingly endless late-career misfires the top honor of the year. Given, anything seems like a better choice when faced with a fellow nominee like Iggy Azalea’s The New Classic, but we digress. Is it Eminem’s worst album? No, see above. Is it good? “Rap God” is certainly a fun listen, but otherwise this punishingly-long album is a clunker.

19. Eminem – ‘Recovery’ (2011)

And the Eminem hits just keep on coming. While no where near the disaster of the albums just previously discussed, Recovery is still another slog of unpleasantness the Grammys deemed worthy of being the year’s definitive rap album. Recovery is at least notable for its pair of chart-conquering smashes – “Love the Way You Lie” can still bang, though “Not Afraid” does not hold up nearly as well now as it did in the summer of 2010.

18. Ludacris – ‘Release Therapy’ (2007)

If Release Therapy had not been the recipient of this award, would anyone have even remembered its existence? Aside from hardcore Ludacris stans and those who pay attention to the iTunes artwork whenever “Money Maker” appears on your nostalgic-pre-game playlist, it seems doubtful that someone could recall this album from memory. For journalism’s sake, we spun this lost treasure to weigh its merits and have come to the following conclusion: Grammy voters were either too wrapped up in the Bush presidency to care about awards or hip-hop had something of a mini Dark Age in 2006.

17. Puff Daddy and the Family – ‘No Way Out’ (1998)

Before the Diddy, before Mr. Combs, and long, long before he was the highest-earning musician for a decade running, he was Puff Daddy. And he announced himself to the world with No Way Out, a debut album that unfortunately finds our hero totally overshadowed by ‘the Family.’ When you stack your guest list with the likes of Notorious B.I.G., Lil’ Kim, JAY-Z and Busta Rhymes, you better have the chops to match – but Puff Daddy gets lost at sea surrounded by such iconic talent.

16. Eminem – ‘The Slim Shady LP’ (2000)

The less we say about Eminem’s actual debut album, the better. For all intents and purposes, this was the birth of the superstar as we know it, ensuring that the name Slim Shady would forever be a cultural force to reckoned with. That the album still sounds so immediately jarring speaks measures to its controversial impact when it arrived in the late winter of 1999; tracks like “97 Bonnie & Clyde” were particularly shocking upon arrival.

15. JAY-Z – ‘Vol. 2… Hard Knock Life’ (1999)

JAY-Z surpassed expectations with his third album proper, delivering a product every bit as thoroughly enjoyable as his first two outings. Only this time around he added some grit to his production (thanks Timbaland, Swiss Beatz et al), perfectly matching his incensed, venomous spitting. This is – somehow – JAY’s only win in the category; that his later efforts (notably, The Blueprint) are some of the greatest albums ever written in any genre escaped the Grammys’ notice.

Listen over on TIDAL.

14. Naughty by Nature – ‘Poverty’s Paradise’ (1996)

Proving that you didn’t have to be raised in NYC to make a name in East Coast ’90s rap (East Orange, New Jersey will do just fine) the tough triumvirate of Naughty by Nature had the unexpected honor of being the first-ever recipients of the Best Rap Album Grammy. Poverty’s Paradise remains a captivating listen, with high-points like the bona fide hit “Feel Me Flow” translating to pure sonic candy.

13. OutKast – ‘Speakerboxxx/The Love Below’ (2004)

Double albums just don’t get any bigger than this; OutKast’s revered symphony of Atlanta hip-hop and go-for-broke pop hits is a colossal achievement, by any measure. With Big Boi and André 3000 taking a disc each to espouse their visions, there is a track for all occasions: be it the gangster boom-bap of “Tomb of the Boom,” the crunk anthem “Last Call,” the silky-smooth bedroom croon of “Roses” or – of course – the universal anthem that can soundtrack weddings, funerals, diners and dance parties alike for time immemorial: “Hey Ya!” The Grammys also named this Album of the Year, one of only two hip-hop albums ever to take the top prize.

12. Eminem – ‘The Eminem Show’ (2003)

Now functioning at the peak of his powers, Academy Award firmly in hand, Eminem was at his most unstoppable around the release of The Eminem Show. And standing at the summit of pop culture, surveying all he saw, Slim Shady was not impressed. Over indelible hits like “Without Me,” “Cleanin’ Out My Closet” and “‘Till I Collapse,” Em delivers one expertly-rhymed critique after another with barely-suppressed glee. Suffice to say, the fun is infectious.

11. Fugees – ‘The Score’ (1997)

Blessed are the Fugees, the holy trinity of Ms. Lauryn Hill, Wyclef Jean and Pras Michel, whose second album – even now, over two decades later – comes close to sublime perfection. As time passes, The Score‘s relevance only continues to grow. Even in the crowded field of today’s hip-hop landscape, you would be hard-pressed to find an album with so many profound realizations of the immigrant experience in America, created by and sung from the voice of the disenfranchised themselves. “Killing Me Softly With His Song” was the monster hit at the time, but plenty more treasures are to be found in the Enya-sampling “Ready or Not” and the loping rhyme-showcase “The Beast.”

10. Chance the Rapper – ‘Coloring Book’ (2017)

Chance the Rapper made history by scooping up a win for Coloring Book last year, becoming the first artist in the award’s history to win for a mixtape. Which is fine and dandy, but that says nothing of the power, dexterity and pure, quality musicianship that flow through each moment of the full-length. Coloring Book is a celebration of life in all its contradictory messiness, with Chance celebrating and luxuriating in the warm radiance of love, friendship and family. Glory be to God indeed.

9. Lil Wayne – ‘Tha Carter III’ (2009)

The story of Lil Wayne and pop culture is a long, winding (and still unfolding) tale. He is unquestionably one of the most talented, innovative MCs to ever pick up a mic, and yet his relevance has waxed and waned without any seeming sense of direction. Tha Carter III however, is the one, perfect moment where Weezy’s prowess, his popularity and his quality converged into one glorious whole. Whether it’s spitting actual fire over the iconic “A Milli” or bringing us all to church on “Let the Beat Build,” this album reminds us why – no matter what he does next – he will always place on a list of the all-time greatest.

8. Kanye West – ‘Graduation’ (2008)

Kanye eschewed the lush orchestration on which he built his sophomore effort Late Registration and dusted off a few 808s for his gloriously-synthetic third album. It speaks to his insane talent that an album like Graduation can rank low on a list of his best work, as this LP plays like something of a greatest-hits album. The chart-topping phenomenon that is “Stronger,” the piercingly-vulnerable synth-glo of “Flashing Lights” and the deliriously-giddy ode to fortune “Good Life” can all qualify as some of Ye’s best tracks, full stop. At this point in his trajectory, it’s fair to say that he did in fact realize he was a champion.

7. Drake – ‘Take Care’ (2013)

When Take Care arrived, it was clear that this was the Drake we were promised. A smattering of Top 40 hits and some intriguing mixtapes hinted at a star in the making, but it was here, on his expertly-curated sophomore album, that Drizzy blossomed. There are hits a plenty in the form of “Headlines” and “HYFR,” but it’s tracks like “Marvin’s Room” that form the bleeding, beating heart of the album, creating the Sadboy Drake we all know and mock now in his most pure, vulnerable form.

6. Eminem – ‘The Marshall Mathers LP’ (2001)

It is no coincidence that Eminem titled his third LP with his given name; this album is not only the skeleton key to unlocking his conflicted, confrontational artistry, but it is a brutally-honest confessional. It is Marshall Mathers as a mortal man, thrust to the heights of celebrity, atoning for every brutal nook and cranny of his disturbed mind and creating intensely human art in the process. “Stan” has yet to be bettered as an example of rap as storytelling, while “Kim” ranks as one of the most disturbing pieces of hip-hop put to tape. Not even the foul sequel he recently made can tarnish this masterwork.

5. Kanye West – ‘The College Dropout’ (2005)

The College Dropout ranks right up there with such legendary records as Ramones or The Velvet Underground & Nico in terms of being a debut album that is not only a singularly flawless execution of an artist’s entire sound but a groundbreaking release that would set the tone for their peers for years to come. That might sound high and mighty, but when was the last time you listened to The College Dropout? Doing so again might remind you that hip-hop as we know it, in many ways, can be traced to this album, right here. A more fitting title would have been The Blueprint, but a certain mentor of Kanye’s had already taken it…

4. Kanye West – ‘Late Registration’ (2006)

And how does Kanye follow such a highwire debut act? By retaining the songcraft, lyrical acrobatics and unadulterated ambition that marked his first record and adding an orchestra. The richly-realized – and even more richly-felt – Late Registration is a masterclass in musicianship, the kind of sophomore album artists would trade their souls in a Faustian bargain to make. Spending a year (and $2 million of his own money) into its creation more than paid off; West’s ambition resulted in such indelible classics as “Hey Mama,” “Diamonds From Sierra Leone” and “Gold Digger,” the latter of which would even now take serious balls to pull off.

3. Kendrick Lamar – ‘To Pimp a Butterfly’ (2016)

The leap forward from Kendrick Lamar’s good kid, m.A.A.d. City to To Pimp a Butterfly is nothing short of astonishing. Where the former was an album that redefined West Coast hip-hop for a new millennium with carefully-written production and an ear for storytelling, the latter is a tapestry of the African-American experience told utilizing every major African-American musical style of the 20th century; a sonic bridge from the slave ships to the ghettos still torn asunder by police brutality. It is among the most vital pieces of art of the African-American experience in any medium. It is loud, it is proud and it is transcendent.

2. OutKast – ‘Stankonia’ (2002)

Speakerboxxx/The Love Below depicted OutKast as irrevocably separate, a duo so divided they needed to make different albums in order to function. Stankonia is OutKast, the duo, at the height of their powers; a blending of the supreme talents of Big Boi and André 3000 so consummate that they would afterward split, never to work so cohesively again. There are of course the songs we can all still recite word for word – “Mrs. Jackson,” “B.O.B.,” “So Fresh, So Clean” – but it is perhaps most important as a living, sonic document of the state of hip-hop in the year 2000. The sounds of an entire region for the genre were all born here; it’s influence is still all around us.

1. Kanye West – ‘My Beautiful Dark Twisted Fantasy’ (2012)

It is amazing to think that Kanye’s Dark Fantasy has not even been with us for 10 years. Its cultural footprint is so pronounced and so immersive that it is something like the Midi-chlorians that sway The Force in hip-hop form; moving through us and surrounding us, always. Never mind that it gave birth to Nicki Minaj as we know it. Never mind that it spawned the intermingling of indie-rock and rap producers that now takes place on any given release. Never mind that it single-handedly saved Kanye from becoming a cultural pariah. It is first and foremost a symphony of grief and grace, the likes of which has never been written before or since, in this century or any other.

Stay tuned for our official Grammy predictions tomorrow. The 60th Annual Grammy Awards air this Sunday, January 28.

  • Cover Image: Abdelhak Senna / AFP / Getty Images
Words by Jake Boyer
Music Editor
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