10. Puff Daddy – No Way Out (1998)
Other nominees: 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
What should have won: Wu-Tang Forever
Before Kanye West and Taylor Swift, there was Ol’ Dirty Bastard and Shawn Colvin. After Puff won the award over both, ODB jumped on stage to announce that “Puffy is good, but Wu-Tang is the best!” No Way Out is a good album that had some classic songs – “Victory,” “Young G’s,” “All About the Benjamins” – but it did not have the power or ambition of either Wu-Tang Forever or Life After Death. For what it’s worth, Charlamagne agrees with me.
9. Jay-Z – Vol. 2…Hard Knock Life (1999)
Other nominees: A Tribe Called Quest – The Love Movement; Big Punisher – Capital Punishment; Jermaine Dupri – Life in 1472; Mase – Harlem World
What should have won: Vol. 2…Hard Knock Life
After the murders of 2Pac and The Notorious B.I.G., there was a void at the top of the game and Jay-Z made the most of his opportunity. Vol. 2… was the album that catapulted him to superstardom, selling more than five million copies and becoming the lone album that gave Jigga a Grammy in the category.
8. Kendrick Lamar – To Pimp a Butterfly (2016)
Other nominees: J. Cole – 2014 Forest Hills Drive; Dr. Dre – Compton; Drake – If You’re Reading This It’s Too Late; Nicki Minaj – The Pinkprint
What should have won: To Pimp a Butterfly
An instant classic, To Pimp a Butterfly is a deep, ambitious, complex album, the sort that is not often found in modern Hip Hop. There was really no other decision and the often-maligned Grammy voters got this one right.
7. Eminem – The Marshall Mathers LP (2001)
Other nominees: DMX – …And Then There Was X; Dr. Dre – 2001; Jay-Z – Vol. 3…Life and Times of S. Carter; Nelly – Country Grammar
What should have won: The Marshall Mathers LP
Determined to avoid the sophomore jinx and armed with angry responses to everyone that dared to voice a negative opinion about him over the previous year, Eminem crafted a brutal, beautiful project that proved he was more than a one-hit wonder or a TRL pop act. Some may believe that 2001 deserved to win, but that album’s production and its hits – “Still D.R.E.,” “The Next Episode” – helped to obscure the fact that the second half of that album is pretty weak, particularly in hindsight. There have been times when Em has won a Grammy without the strongest album in the field, but this was not one of them.
6. Kanye West – Late Registration (2006)
Other nominees: 50 Cent – The Massacre; Common – Be; Missy Elliott – The Cookbook; Eminem – Encore
What should have won: Late Registration
Late Registration is the last version of Kanye before he became something else. It is ambitious without being in love with its own ambition, featuring great songs, great lines, and great guest spots. It’s a bit too long, but still far better than its competition. Not even those Em stans at the Grammys could argue in favor of Encore.
5. Kanye West – The College Dropout (2005)
Other nominees: Beastie Boys – To the 5 Boroughs; Jay-Z – The Black Album; LL Cool J – The DEFinition; Nelly – Suit
What should have won: The College Dropout
A Hip Hop artist unlike any we had ever seen released an album unlike anything we had ever heard. It’s funny and heartfelt, honest yet optimistic. The Black Album is great (even with “Justify My Thug”), but in its sprawl, The College Dropout is able to show its uniqueness and creativity.
4. Eminem – The Eminem Show (2003)
Other nominees: Ludacris – Word of Mouf; Mystikal – Tarantula; Nelly – Nellyville; Petey Pablo – Diary of a Sinner: 1st Entry
What should have won: The Eminem Show
A very weak field combined with probably Em’s best album made this a no-brainer.
3. Outkast – Stankonia (2002)
Other nominees: Eve – Scorpion; Ja Rule – Pain is Love; Jay-Z – The Blueprint; Ludacris – Back for the First Time
What should have won: The Blueprint
Stankonia is a great album. It is a complete, fully realized project with several classic singles – “So Fresh, So Clean,” “Ms. Jackson,” “B.O.B.” It is one of the best albums to ever win this award…but it’s still not as good or as important as The Blueprint. Jay-Z’s magnum opus, with its use of ’70s soul samples, classic diss track (“The Takeover”), and legendary lone guest appearance (Eminem on “Renegade”), was a high point for the game’s biggest artist and lived up to its title by setting the foundation of the sound of the genre for the next few years.
2. Kanye West – Graduation (2008)
Other nominees: Common – Finding Forever; Jay-Z – Kingdom Come; Nas – Hip Hop is Dead; T.I. – T.I. vs. T.I.P.
What should have won: Graduation
If you ever need proof that the Grammy selection process for Best Rap Album is determined by commercially relevant songs and well-known artists, look no further than the list of nominees from 2008. Three stars – Jay-Z, Nas, and T.I. – were nominated for projects that ranged from wack to super wack. Fortunately, Kanye had unleashed one of his best, the album on which he pivoted from rap star to music star. It has a song for every mood and locale – “Can’t Tell Me Nothing,” “Stronger,” “Champion,” “Good Life” – and proved that Kanye was still getting better.
1. Kanye West – My Beautiful Dark Twisted Fantasy (2012)
Other nominees: Lupe Fiasco – Lasers; Jay-Z and Kanye West – Watch the Throne; Nicki Minaj – Pink Friday; Lil Wayne – Tha Carter IV
What should have won: My Beautiful Dark Twisted Fantasy
The best album by the most important artist of the century, My Beautiful Dark Twisted Fantasy is a masterpiece. No one is making albums like this – not even Kanye. Even for a group as out-of-touch as Grammy voters, this choice was clear.
Other nominees: 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
What should have won: Wu-Tang Forever
Before Kanye West and Taylor Swift, there was Ol’ Dirty Bastard and Shawn Colvin. After Puff won the award over both, ODB jumped on stage to announce that “Puffy is good, but Wu-Tang is the best!” No Way Out is a good album that had some classic songs – “Victory,” “Young G’s,” “All About the Benjamins” – but it did not have the power or ambition of either Wu-Tang Forever or Life After Death. For what it’s worth, Charlamagne agrees with me.
9. Jay-Z – Vol. 2…Hard Knock Life (1999)
Other nominees: A Tribe Called Quest – The Love Movement; Big Punisher – Capital Punishment; Jermaine Dupri – Life in 1472; Mase – Harlem World
What should have won: Vol. 2…Hard Knock Life
After the murders of 2Pac and The Notorious B.I.G., there was a void at the top of the game and Jay-Z made the most of his opportunity. Vol. 2… was the album that catapulted him to superstardom, selling more than five million copies and becoming the lone album that gave Jigga a Grammy in the category.
8. Kendrick Lamar – To Pimp a Butterfly (2016)
Other nominees: J. Cole – 2014 Forest Hills Drive; Dr. Dre – Compton; Drake – If You’re Reading This It’s Too Late; Nicki Minaj – The Pinkprint
What should have won: To Pimp a Butterfly
An instant classic, To Pimp a Butterfly is a deep, ambitious, complex album, the sort that is not often found in modern Hip Hop. There was really no other decision and the often-maligned Grammy voters got this one right.
7. Eminem – The Marshall Mathers LP (2001)
Other nominees: DMX – …And Then There Was X; Dr. Dre – 2001; Jay-Z – Vol. 3…Life and Times of S. Carter; Nelly – Country Grammar
What should have won: The Marshall Mathers LP
Determined to avoid the sophomore jinx and armed with angry responses to everyone that dared to voice a negative opinion about him over the previous year, Eminem crafted a brutal, beautiful project that proved he was more than a one-hit wonder or a TRL pop act. Some may believe that 2001 deserved to win, but that album’s production and its hits – “Still D.R.E.,” “The Next Episode” – helped to obscure the fact that the second half of that album is pretty weak, particularly in hindsight. There have been times when Em has won a Grammy without the strongest album in the field, but this was not one of them.
6. Kanye West – Late Registration (2006)
Other nominees: 50 Cent – The Massacre; Common – Be; Missy Elliott – The Cookbook; Eminem – Encore
What should have won: Late Registration
Late Registration is the last version of Kanye before he became something else. It is ambitious without being in love with its own ambition, featuring great songs, great lines, and great guest spots. It’s a bit too long, but still far better than its competition. Not even those Em stans at the Grammys could argue in favor of Encore.
5. Kanye West – The College Dropout (2005)
Other nominees: Beastie Boys – To the 5 Boroughs; Jay-Z – The Black Album; LL Cool J – The DEFinition; Nelly – Suit
What should have won: The College Dropout
A Hip Hop artist unlike any we had ever seen released an album unlike anything we had ever heard. It’s funny and heartfelt, honest yet optimistic. The Black Album is great (even with “Justify My Thug”), but in its sprawl, The College Dropout is able to show its uniqueness and creativity.
4. Eminem – The Eminem Show (2003)
Other nominees: Ludacris – Word of Mouf; Mystikal – Tarantula; Nelly – Nellyville; Petey Pablo – Diary of a Sinner: 1st Entry
What should have won: The Eminem Show
A very weak field combined with probably Em’s best album made this a no-brainer.
3. Outkast – Stankonia (2002)
Other nominees: Eve – Scorpion; Ja Rule – Pain is Love; Jay-Z – The Blueprint; Ludacris – Back for the First Time
What should have won: The Blueprint
Stankonia is a great album. It is a complete, fully realized project with several classic singles – “So Fresh, So Clean,” “Ms. Jackson,” “B.O.B.” It is one of the best albums to ever win this award…but it’s still not as good or as important as The Blueprint. Jay-Z’s magnum opus, with its use of ’70s soul samples, classic diss track (“The Takeover”), and legendary lone guest appearance (Eminem on “Renegade”), was a high point for the game’s biggest artist and lived up to its title by setting the foundation of the sound of the genre for the next few years.
2. Kanye West – Graduation (2008)
Other nominees: Common – Finding Forever; Jay-Z – Kingdom Come; Nas – Hip Hop is Dead; T.I. – T.I. vs. T.I.P.
What should have won: Graduation
If you ever need proof that the Grammy selection process for Best Rap Album is determined by commercially relevant songs and well-known artists, look no further than the list of nominees from 2008. Three stars – Jay-Z, Nas, and T.I. – were nominated for projects that ranged from wack to super wack. Fortunately, Kanye had unleashed one of his best, the album on which he pivoted from rap star to music star. It has a song for every mood and locale – “Can’t Tell Me Nothing,” “Stronger,” “Champion,” “Good Life” – and proved that Kanye was still getting better.
1. Kanye West – My Beautiful Dark Twisted Fantasy (2012)
Other nominees: Lupe Fiasco – Lasers; Jay-Z and Kanye West – Watch the Throne; Nicki Minaj – Pink Friday; Lil Wayne – Tha Carter IV
What should have won: My Beautiful Dark Twisted Fantasy
The best album by the most important artist of the century, My Beautiful Dark Twisted Fantasy is a masterpiece. No one is making albums like this – not even Kanye. Even for a group as out-of-touch as Grammy voters, this choice was clear.
