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*


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
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.


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
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.


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
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.


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
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.


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

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.


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
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.


Original Nominees and Winner
Eve – Scorpion
Ja Rule – Pain Is Love
Jay-Z – The Blueprint
Ludacris – Back for the First Time
OutKast - Stankonia

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.


Original Nominees and Winner
Ludacris – Word of Mouf
Mystikal – Tarantula
Nelly – Nellyville
Petey Pablo – Diary of a Sinner: 1st Entry
Eminem - The Eminem Show
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.


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
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.


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
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.


Original Nominees and Winner
50 Cent – The Massacre
Common – Be
Missy Elliott – The Cookbook
Eminem – Encore
Kanye West - Late Registration
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.


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
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.


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
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.


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
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.


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
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.


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
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.


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
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.


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
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.


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
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 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
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.