A Look Into The Grammy’s Best Rap Award From Beginning Till Date


Lets face it, when
it comes to Hip Hop and Rap in general, the Grammy Awards have proven
time and again that it doesn’t truly understand the genre. Upsets in the
nomination and award presenting process have provided us a wonderful idea.

Just in time for the coveted awards ceremony, we’ve decided to
rewrite Hip Hop’s history with The Grammys by providing an alternative
take on who should have been nominated and won the highly regarded prize
– Best Rap Album. Doing our best to stay within each year’s guidelines
for eligibility, the list represents a version of what
mainstream’s view of the culture could have been.

So, while last year we gave you a year by year breakdown of who we
would have picekd to take the prize, this year we went ahead and
reworked the entire category, both picking the albums we think should
have gotten nominated and picking our winners from that pool of
applicants. At times the differences are stark and at others we mostly
agreed with the Grammy committee’s thinking, but, either way, we gave
you a reimagining of events had they gone the way (maybe) Hip Hop would
have liked them too.

Disclaimer: Because Grammy Award rules changes year-by-year, albums released years prior are eligible. For example, while Kendrick Lamar’s Good Kid m.A.A.d City was
released in late 2012, the release was nominated for 2014. Though the
usual dates for eligibility are October 1 to September 30, the 2011
Grammys pushed the date up from September 1 to September 30. This is why
Jay Z’s The Blueprint 3 was released September 8, 2009 but was
eligible for the 2011 ceremonies. Also taken into consideration were
changes to the number of nominees. For 2013, six nominees for Best Rap
Album made made the running outside of the usual five.

*Winners Bold & Italicized*

1996

grammy

Original Nominees and Winner

2Pac – Me Against the World

Bone Thugs-n-Harmony – E 1999 Eternal

Ol’ Dirty Bastard – Return to the 36 Chambers: The Dirty Version

Skee-Lo – I Wish

Naughty By Nature – Poverty’s Paradise

HipHopDX

The Roots – Do You Want More??

Raekwon – Only Built 4 Cuban Linx

Bone Thugs-n-Harmony – E 1999 Eternal (Ural)

Mobb Deep – The Infamous

Ol’ Dirty Bastard – Return to the 36 Chambers: The Dirty Version (Andre)

Ural: The real fight should have been between Mobb Deep’s The Infamous and Bone Thugs-N-Harmony E 1999 Eternal.
Both were hauntingly visceral but the delivery catapulted Bone Thugs to
the top. What the Eazy-E protegees did was essentially create a top
tier hood horror movie.

Andre: Of course I’d like to choose Mobb Deep’s The Infamous, but my pick was Ol Dirty’s Return to the 36 Chambers: The Dirty Version.
Solipsistic and raucous and utterly ahead of his time, Dirty introduced
the Drunken master style of Rap to Hip Hop, which in turn spawned Lil
Wayne and his spiritual progeny Young Thug.

1997

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Original Nominees and Winner

2Pac – All Eyez On Me

A Tribe Called Quest – Beats, Rhymes & Life

Coolio – Gangsta’s Paradise

LL Cool J – Mr. Smith

Fugees – The Score

HipHopDX

Jay Z – Reasonable Doubt

OutKast – ATLiens

Fugees – The Score (Ural)

Nas – It Was Written (Andre)

2Pac – All Eyez On Me

Ural: The Score was an easy sweep that year. However,
adding OutKast’s ATLiens to the mix would have made an interest matchup
as both represented two interesting directions for Hip Hop. However,
Outkast wouldn’t get their true footing until Aquemini as ATLiens felt like an experiment regardless of how good it was. The Score was a clear fusing of great spitting from all members plus amazing singing from Lauryn and slick production.

Andre: Nas’ It Was Written was not well received when
it was released in 1996. Yeah, it got four mics in The Source, but the
Trackmasters production was not what people expected from the man who
worked primarily with Large Pro, Tip, and Premo to great effect. Either
way, it’s grown to be regarded as arguably Nas’ best work. A tougher,
prodigious and more accessible version of the New York original and well
deserving of that years Grammy award.

1998

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Original Nominees and Winner

Missy Elliott – Supa Dupa Fly

Wyclef Jean – Wyclef Jean Presents The Carnival

The Notorious B.I.G. – Life After Death

Wu-Tang Clan – Wu-Tang Forever

Puff Daddy & The Family – No Way Out

HipHopDX

Camp Lo – Uptown Saturday Night

Common – One Day It’ll All Make Sense

Wu-Tang Clan – Wu-Tang Forever

The Notorious B.I.G. – Life After Death (Andre)

Missy Elliott – Supa Dupa Fly (Ural)

Ural: Lets not act like Supa Dupa Fly didn’t sonically
pushed Hip Hop in a bold direction that still permeates the culture
today. Missy’s vocal flips between singing and rapping only added to
Timbaland’s groundbreaking production.

Andre: Life After Death was a double disc buffet. And
while B.I.G. squeezed it to make it fit, the sonic experimentation and
cleverness throughout made you think you were listening to the best
movie ever. “Playa Hater” was also the nicest way of saying “you’ve been
robbed” of all time.

1999

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Original Nominees and Winner

A Tribe Called Quest – The Love Movement

Big Punisher – Capital Punishment

Jermaine Dupri – Life in 1472

Mase – Harlem World

Jay Z – Vol 2…A Hard Knock Life

HipHopDX

OutKast – Aquemini (Both)

Gang Starr – Moment of Truth

Jay Z – Vol 2…A Hard Knock Life

Beastie Boys – Hello Nasty

DMX – It’s Dark and Hell is Hot

Ural: Vol 2… A Hard Knock Life was clearly Hov’s
first crossover moment. However, Big Boi and Andre 3K managed to give
ATLien’s experimentation a clear vision and the world was made better in
the process. “SpottieOttieDopaliscious” anyone?

Andre:  Aquemini. It might be the best album of the decade, period.

2000

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Original Nominees and Winner

Busta Rhymes – E.L.E. (Extinction Level Event): The Final World Front

Missy Elliott – Da Real World

Nas – I Am…

The Roots – Things Fall Apart

Eminem – The Slim Shady LP

HipHopDX

Mos Def – Black On Both Sides

The Roots – Things Fall Apart (Ural)

Eminem – The Slim Shady LP (Andre)

Method Man and Redman – Blackout

Pharoahe Monch – Internal Affairs

Ural: There’s no doubt that Eminem is one of the greatest lyricists in Hip Hop. However, his real moment wouldn’t be until The Marshall Mathers LP. This is where Things Fall Apart climbs as the Philly collective’s best example of strong instrumentation and Black Thought’s poignant lyricism.

Andre:  The Slim Shady LP was ridiculously shady. In
fact, this album was when “Shady” reigned supreme. His other alters
would show in time, but for now the zany antics of this egomaniacal baby
would take the world by storm.

2001

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Original Nominees and Winner

DMX – …And Then There Was X

Dr. Dre – 2001

Jay-Z – Vol. 3… Life and Times of S. Carter

Nelly – Country Grammar

Eminem – The Marshall Mathers LP

HipHopDX

Q-Tip – Amplified

Dr. Dre – 2001 (Andre)

Eminem – The Marshall Mathers LP (Ural)

Common – Like Water for Chocolate

Ghostface Killah – Supreme Clientele

Ural: If The Slim Shady LP was a warm-up, The Marshall Mathers LP clearly had Eminem at gametime. Clearly, nothing was touching it regardless of anything released in the period.

Andre:  It’s a compilation, but it’s more than that, right?
Mostly, it’s a bunch prodigious posse cuts molded to perfection. Again,
here, Dre´ pulled off a West Coast miracle. And while Supreme Clientele is arguably Ghost’s best work, it doesn’t quite match the sheer force of 2001.

2002

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Original Nominees and Winner

Eve – Scorpion

Ja Rule – Pain Is Love

Jay-Z – The Blueprint

Ludacris – Back for the First Time

OutKast – Stankonia

HipHopDX

OutKast – Stankonia (Ural)

Jay-Z – The Blueprint (Andre)

Missy Elliott – Miss E… So Addictive

Ja Rule – Pain Is Love

Reflection Eternal – Train of Thought

Ural: Like it or not, Hip Hop’s current union with EDM can be traced to Miss E… So Addictive. The Blueprint was Hov’s realization as something more than being the best rapper alive. Stankonia
gave music in general a progressive space odyssey smothered in southern
style gravy. OutKast officially repaved their lane for a future
follow-up that would change Hip Hop forever and deserved the win.

Andre:  The Blueprint was Hov’s magnum opus, and as good as Stankonia was, the album that launched Jay Z into the stratosphere deserves the win here.

2003

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Original Nominees and Winner

Ludacris – Word of Mouf

Mystikal – Tarantula

Nelly – Nellyville

Petey Pablo – Diary of a Sinner: 1st Entry

Eminem – The Eminem Show

HipHopDX

Nas – Stillmatic (Andre)

Eminem – The Eminem Show

Blackalicious – Blazing Arrow

Cee-Lo Green – Cee-Lo Green and His Perfect Imperfections (Ural)

Talib Kweli – Quality

Ural: Eminem, Nas, Talib Kweli and Blackalicious (Gift of Gab
and Chief Xcel) contributed to one heavily lyrical year. Going out on a
limb, Cee-Lo Green and His Perfect Imperfections felt like the
perfect appetizer to what OutKast would separately cook up a year later.
The same now creepy Goodie Mob member who joined Danger Mouse for
Gnarls Barkley and managed to make “F You” a hit single made a
criminally slept on solo debut. This is why Cee-Lo deserved the award
that year without a doubt.

Andre: “Fuck Jay Z!” And with that Nas sent the shot heard
round the world. He then followed up with an album good enough to be the
namesake of his original classic LP and Nasty Nas was reborn. So for my
money Nas is the winner here.

2004

posterartwk_2004_046

Original Nominees and Winner

50 Cent – Get Rich or Die Tryin’

Missy Elliott – Under Construction

Jay-Z – The Blueprint 2: The Gift & the Curse

The Roots – Phrenology

OutKast – Speakerboxxx/The Love Below

HipHopDX

50 Cent – Get Rich or Die Tryin’ (Andre)

Missy Elliott – Under Construction

OutKast – Speakerboxxx/The Love Below (Ural)

The Roots – Phrenology

Bubba Sparxxx – Deliverance

Ural: Attempting to understand why The Gift & the Curse even made the running outside of being a Jay Z album, the line-up would have been fierce if Bubba Sparxxx’s Deliverance was the replacement. However, nothing was going to stopping the behemoth of Speakerboxxx/The Love Below.

Andre:  In a sane Grammy world, Outkast gets the nod for Aquemini and Stankonia and
leaves the winners circle empty for 50 Cent to get the Grammy award for
his classic. So, since we’re making this up ourselves, King Fif’ has to
take home the prize for his diamond selling LP.

2005

posterartwk_2005_047

Original Nominees and Winner

Beastie Boys – To the 5 Boroughs

Jay-Z – The Black Album

LL Cool J – The DEFinition

Nelly – Suit

Kanye West – The College Dropout

HipHopDX

Beastie Boys – To the 5 Boroughs

Jay-Z – The Black Album

Kanye West – The College Dropout (Andre)

Madvillain – Madvillainy (Ural)

Twista – Kamikaze

Ural: Kanye West’s solo debut may have been a favorite by the vast majority but real Hip Hop heads always looked to Madvillainy
as the greatest representation within the genre. Madlib at the time
dominated on the production side and MF Doom was a dangerous emcee.
Regardless of how phenomenal The College Dropout was, it pailed in comparison to Madvillainy.

Andre: As great as Madvillainy was and continues to be listen after dangerous listen, The College Dropout
was the very first time Hip Hop went middle class. The guy talked about
working at the Gap and assaulting his boss, and somehow, it wasn’t
corny or ridiculous. Instead it was relatable and triumphant.

2006

posterartwk_2006_048

Original Nominees and Winner

50 Cent – The Massacre

Common – Be

Missy Elliott – The Cookbook

Eminem – Encore

Kanye West – Late Registration

HipHopDX

Common – Be

Kanye West – Late Registration (Ural)

The Game – The Documentary (Andre)

Eminem – Encore

Lil Brother – The Minstrel Show

Ural: Late Registration was officially the true beginning of Kanye West’s dominance. Hell, outside of Encore and The Massacre, Ye literally had a hand in some form on both Be and The Documentary which was way better than Missy’s The Cookbook. If The College Dropout was the grand introduction to the rapper/producer, Late Registration was the sophomore follow-up most pray for.

Andre: As far as favorite Ye´albums go, Late Registration is my cinnamon apple. However, The Game’s The Documentary served
up a healthy helping of 50, The Game, and Dr. Dre. So while it was
nothing new, it was a flawlessly executed gem that should have earned
Game a Grammy Award.

2007

posterartwk_2007_049

Original Nominees and Winner

Lupe Fiasco – Lupe Fiasco’s Food & Liquor

Pharrell – In My Mind

The Roots – Game Theory

T.I. – King

Ludacris – Release Therapy

HipHopDX

Lupe Fiasco – Lupe Fiasco’s Food & Liquor (Ural)

The Roots – Game Theory

Lil Wayne – Tha Carter II (Andre)

T.I. – King

Ghostface Killah – Fishscale

Ural: One of the bigger upsets in Grammy history, Lupe Fiasco was robbed by Ludacris’ failed reinvention Release Therapy. In fact, that album shouldn’t have even been in consideration. Though Wayne gratefully reached another plateau of lyricism, Lupe Fiasco’s Food & Liquor was already miles ahead.

Andre:  Lil Wayne’s best album is arguably Tha Carter II. In fact, although Tha Carter III was experimentally and commercially successful, and Lupe’s debut blew open the doors on keen, nerdy Rap introspection, Tha Carter II is what set of Wayne’s run of 2000s Rap dominanance. And, of all that, it is still in my mind his best work.

2008

posterartwk_2007_051

Original Nominations and Winner

Common – Finding Forever

Jay-Z – Kingdom Come

Nas – Hip Hop Is Dead

T.I. – T.I. vs. T.I.P.

Kanye West – Graduation

HipHopDX

The Clipse – Hell Hath No Fury (Both)

Kanye West – Graduation

Common – Finding Forever

Pharoahe Monch – Desire

Blu & Exile – Below The Heavens

Ural: Graduation was another great body of work from Kanye West but better than Hell Hath No Fury? No way. The Clipse turned drug nihilism on its head and The Neptunes provided the haunting soundtrack.

Andre:  The Clipse achievement, Hell Hath No Fury was a stone-cold thrill ride. There’s a soft spot in our hearts for Blu & Exile’s Below The Heavens, though, the sweetest and most emotionally honest Hip Hop album of the aughts (it’s a toss up between that and 808’s & Heartbreak), but the VA natives drug slander over Neptunes production deserved the award.

2009

posterartwk_2008_050

Original Nominations and Winner

Jay-Z – American Gangster

Lupe Fiasco – Lupe Fiasco’s The Cool

Nas – Untitled

T.I. – Paper Trail

Lil Wayne – Tha Carter III

HipHopDX

Jay-Z – American Gangster

Lupe Fiasco – Lupe Fiasco’s The Cool (Both)

T.I. – Paper Trail

Lil Wayne – Tha Carter III

The Roots – Rising Down

Ural: Lil Wayne’s breakout moment in Tha Carter III
officially gave him room to truly call himself one of Hip Hop’s elites.
However, Lupe Fiasco created a darker, more focused conceptual work and
overall better album through The Cool.

Andre:  The Cool is Lupe’s The Blueprint,
but conceptual, dark, and political without falling over into folly.
And while his future projects would be marred by label troubles and
variant, sardonic Twitter exchanges, The Cool was almost a perfect representation of Lupe’s mind, and a flawless victory.

2010

posterartwk_2010_052

Original Nominations and Winner

Common – Universal Mind Control

Flo Rida – R.O.O.T.S.

Mos Def – The Ecstatic

Q-Tip – The Renaissance

Eminem – Relapse

HipHopDX

Mos Def – The Ecstatic (Ural)

Q-Tip – The Renaissance

Eminem – Relapse

Kid Cudi – Man On The Moon: The End of Day

Kanye West – 808’s & Heartbreak (Andre)

Ural: Though Eminem’s Relapse was the first album released from Shady in quite some time, it couldn’t hold up against The Renaissance let alone The Ecstatic. Mos Def (now Yasiin Bey) created a painting that’s sonically rich and thankfully, strains everything wrong with The New Danger and True Magic.
When it comes to the an album featuring the best blending of
musicality, singing and straight rhyming, even Kanye’s emotional
exercise couldn’t stop The Ecstatic.

Andre:  Kanye West’s 808s & Heartbreak was an
emotional tour de force, and it suffered mightily from the Hip Hop
climate and its late post-Grammy consideration release. In time, many of
us would come to understand the importance of 808s and the lane it
created for the likes of future emcees like Drake and Childish Gambino.
As one of the most important albums of the previous decade, of course it
deserved a Grammy award.

2011

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Original Nominations and Winner

B.o.B – B.o.B Presents: The Adventures of Bobby Ray

Drake – Thank Me Later

Jay-Z – The Blueprint 3

The Roots – How I Got Over

Eminem – Recovery

HipHopDX

The Roots – How I Got Over

Eminem – Recovery

Jay-Z – The Blueprint 3

Big Boi – Sir Lucious Left Foot: The Son of Chico Dusty (Both)
Drake – Thank Me Later
Ural: Pulling aside the acclaim of The Roots, Eminem and Jay
-Z, their better days felt beyond them in terms of their albums being
candidates. By the time Drake’s solo hit shelves, it was seen as a total
disappointment. 2010 was the year Big Boi finally stepped out of Andre
3K’s “Hey Ya” shadow with the incredible and award deserving Sir Lucious Left Foot: The Son of Chico Dusty.

Andre: Sir Lucious Left Foot never step foot in the shadow of
Andre 3K. His greatness is cemented albeit differently, and he is a Hip
Hop legend for that reason. On this album, Big Boi went left again after
Speakerboxxx crafting a dungeon family experience that could absolutely not be copied. Therefore, Big Boi grabs the award.

2012

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Original Nominations and Winner

Lupe Fiasco – Lasers

Jay-Z and Kanye West – Watch the Throne

Nicki Minaj – Pink Friday

Lil Wayne – Tha Carter IV

Kanye West – My Beautiful Dark Twisted Fantasy

HipHopDX

Jay-Z and Kanye West – Watch the Throne

Kanye West – My Beautiful Dark Twisted Fantasy (Both)

Tyler The Creator – Goblin

Lil Wayne – Tha Carter IV

Kid Cudi – Man On The Moon II: The Legend of Mr. Rager

Ural: Yeezy’s epic comeback through My Beautiful Dark Twisted Fantasy managed to be the most talked about rap album of the year. Everything else was just, well, great.

Andre:  MBDTF is up for best Hip Hop album of all-time.
It is an almost flawless project thematically, sonically and a
timestamp for Hip Hop. Of course, it also deserves the Grammy.

2013

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Original Nominations and Winner

2 Chainz – Based on a T.R.U. Story

Lupe Fiasco – Food & Liquor II: The Great American Rap Album Pt. 1

Nas – Life Is Good

Rick Ross – God Forgives, I Don’t

The Roots – Undun

Drake – Take Care

HipHopDX

Nas – Life Is Good

The Roots – Undun (Andre)

Drake – Take Care (Ural)

Killer Mike & El P – R.A.P. Music

Big K.R.I.T. – Live from the Underground

Big Boi – Vicious Lies and Dangerous Rumors

Ural: After a somewhat disappointing debut, Drake came the following year with his opus Take Care.
The album that transitioned the Toronto native officially to the big
leagues and became a turning point while crafting something that
overtook his peers.

Andre: Undun was a masterpiece that saw the most experimental Hip Hop group of the past decade went even further left with Undun, creating a vacuum of creative energy that still hasn’t been filled. Not even by themselves.

2014

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Original Nominations and Winner

Drake – Nothing Was the Same

Jay-Z – Magna Carta Holy Grail

Kendrick Lamar – Good Kid, M.A.A.D City

Kanye West – Yeezus

Macklemore and Ryan Lewis – The Heist

HipHopDX

Drake – Nothing Was the Same

Kendrick Lamar – Good Kid, M.A.A.D City (Both)

Kanye West – Yeezus

J Cole – Born Sinner

Macklemore and Ryan Lewis – The Heist

Ural: Besides the obvious of who really should have really
won. Kendrick Lamar’s debut was utter perfection for many and a game
changer. Being more specific, J Cole’s Born Sinner was a better project than his mentor’s twelfth studio album. But damn it if Good Kid, M.A.A.D City isn’t the best album of the decade so far.

Andre:  Good Kid, M.A.A.D City was robbed that night, and I won’t be doing that again. Kendrick’s debut gets the nod over anything that year.

2015

2015 Grammy

Original Nominations

Iggy Azalea – The New Classic

Common – Nobody’s Smiling

Eminem – The Marshall Mathers LP 2

Childish Gambino – Because the Internet

Wiz Khalifa – Blacc Hollywood

ScHoolboy Q – Oxymoron

HipHopDX

YG – My Krazy Life

Run The Jewels – Run the Jewels 2 (Ural)

Future – Honest

ScHoolboy Q – Oxymoron

Childish Gambino – Because the Internet (Andre)

Eminem – The Marshall Mathers LP 2

Ural: Besides excluding YG’s My Krazy Life, leaving Run The Jewels 2 and Future’s Honest
out of the lineup didn’t make a lick of sense. If Killer Mike and El P
were in the running, all other conversations regarding race’s role in
Grammy Best Rap Album discussion wouldn’t be much of an issue. Plus, it
was just better than anything in this year’s list.

Andre: Childish Gambino’s textured Rap-as-Pop-art showing in 2013 went starkly different places from his Pitchfork ethered Camp.
It featured a weirdo script and a lense into the blithe monotony of his
meanderings. It was also super-powerful because of it, and it deserves
this year’s Grammy.

Andre Grant is an NYC native turned L.A. transplant that has
contributed to a few different properties on the web and is now the
Features Editor for HipHopDX. He’s also trying to live it to the limit
and love it a lot. Follow him on Twitter
@drejones.

Ural Garrett is an Los Angeles-based journalist and HipHopDX’s
Senior Features Writer. When not covering music, video games, films and
the community at large, he’s in the kitchen baking like Anita. Follow
him on Twitter
@Uralg.

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