Considered the biggest night of the year in music, the award show celebrates the best that the industry has to offer, giving out accolades for individual songs and albums alike, across a multitude of genres.

While the Grammy Awards usually grab the spotlight just because it’s a cultural institution, this year, the ceremony will be particularly buzz worthy due to the stiff competition in the major categories. Artists including JAY-Z, Kendrick Lamar, Childish Gambino and Bruno Mars are vying for awards like Album of the Year, Record of the Year, and Song of the Year.
This year’s Grammy Awards may mark the first year that hip-hop has been truly accepted by the voting committee and given its due respect as a global force. In past times, the Grammy’s relationship with the culture has been tenuous at best.
In 1989, the award for Best Rap Performance was first presented at the 31st Annual Grammy Awards. However, the recipients, DJ Jazzy Jeff & The Fresh Prince, would boycott the show, along with other nominees including Salt-N-Pepa, LL Cool J and JJ Fad, due to the awards presentation not being televised.
Things would improve over the years, with the Grammy Awards embracing rap artists like Arrested Development, Lauryn Hill, Diddy, JAY-Z, Eminem, and Kanye West, but in many instances, the committee’s decisions as to who was worthy of awards often conflicted with the hip-hop community’s, particularly in the case of the award for Best Rap Album.
First introduced at the 38th Annual Grammy Awards in 1996, the Best Rap Album award has crowned deserving albums like The Fugees’ The Score, Outkast’s Stankonia, and Kanye West’s The College Dropout. But there have been multiple instances in which the Grammys simply got it wrong.
The Boombox delved deep into the history books and selected 10 classics that should have won a Grammy award for Best Rap Album, but didn’t.

10 Albums That Deserved Grammy Awards for Best Rap Album

Bone Thugs-N-Harmony, ‘E. 1999 Eternal’

The first misstep by the Grammy committee concerning Best Rap Album occurred at the 38th Annual Grammy Awards in 1996, when Naughty by Nature’s Poverty’s Paradise won over Bone Thugs-N-Harmony’s E. 1999 Eternal. Housing smash singles like “1st of tha Month” and “Tha Crossroads,” ‘E. 1999 Eternal’ was certainly more than deserving over a Naughty By Nature album that came after their peak during the early ’90s.

The Notorious B.I.G., ‘Life After Death’

The year of rap in 1997 was defined by the murder of The Notorious B.I.G. and the rise of Puff Daddy the artist, making it one of the more unforgettable in the genre’s history. At the 40th Annual Grammy Awards, Puff Daddy’s No Way Out album would beat out The Notorious B.I.G.’s swan song, Life After Death. But with the passage of time, it’s clear that the latter is the superior body of work and one that holds more weight culturally 20 years later.

Big Pun, ‘Capital Punishment’

Vol 2… Hard Knock Life, JAY-Z’s third studio album, dominated the field in 1998, topping out at over 5 million copies sold and signaling the coronation of Jigga as the new King of New York. However, upon closer examination, one album release from that year that has gone on to trump Vol. 2. in terms of staying power and sheer quality is Big Pun’s 1998 debut, Capital Punishment. Combining hit singles and brooding deep cuts, the Bronx bomber put on a tutorial that even your favorite rapper could only marvel at.

The Roots, Things Fall Apart’

Eminem’s meteoric rise was undeniable and captivating, which helped him snag Best Rap Album at the 42nd Annual Grammy Awards for his 1999 debut, Slim Shady LP. On the other hand, The Roots were closer to critical darlings than superstars, making them inherent underdogs when pitted against 8 Mile’s favorite son. But when you check the tale of the tape, Things Fall Apart may arguably be the pinnacle of The Roots’ career and is undoubtedly a masterpiece, which gives it the edge over Slim Shady LP.

50 Cent, ‘Get Rich or Die Tryin’

In 2004, at the 46th Annual Grammy Awards, the biggest snubs were definitely attributed to 50 Cent, who dominated 2003 off the strength of his multi-platinum debut, Get Rich or Die Tryin’. Aside from losing out in the Best New Artist category to Evanesence, the G-Unit general was also denied the Best Rap Album award, which was given to Outkast’s Speakerboxxx/The Love Below. While a fan and critical favorite, Speakerboxx took home the coveted Best Album Award that year– a landmark for hip-hop. That should’ve freed up space for 50 Cent’s debut album, which was deserving of the Best Rap nod.

T.I., ‘King’

Ludacris finally earned the artistic respect he craved after winning Best Rap Album at the 49th Annual Grammy Awards for his album Release Therapy, but his victory came at the expense of rival T.I., who had unleashed a career defining effort with his fourth studio album, King, in 2006. “What You Know,” “Why You Wanna” and “Top Back (Remix)” are enough reason to give King the edge, but when you add in album cuts like “I’m Talkin’ to You” and “Get It,” among others, it becomes more clear that King was the victim of a robbery.

Q-Tip, ‘The Renaissance’

One of the years in which the competition for Best Rap Album was less stiff than usual, Eminem walked away with the win with his sixth studio album, Relapse, giving the rapper his fourth victory in the category. Despite being considered a comeback album of sorts for Em, the album that was more deserving was Q-Tip’s 2009 offering The Renaissance, a superb longplayer that reminded listeners the Abstract was still as good as they come at painting pictures over loops and beats.

The Roots, ‘How I Got Over’

The 53rd Annual Grammy Awards (2010) would include yet another notch on Eminem’s belt with his fifth win in the Best Rap Album category, extending his record. However, the win was one of the more egregious cases of the Grammy’s getting it wrong, overlooking blockbuster albums like Drake’s Thank Me Later, and more importantly, The Roots’ How I Got Over, an album that is devoid of flaw and one of the standouts in their illustrious catalog.

Kendrick Lamar, Good Kid, Maad City’

At the 56th Annual Grammy Awards in 2014, Macklemore & Ryan Lewis’ The Hesist would win over Kendrick Lamar’s Good Kid, M.A.A.D. City in arguably the most controversial decision in Best Rap Album history. The backlash as a result of the decision was so harsh that Macklemore himself went on record as saying that Good Kid, M.A.A.D. City was more deserving of the honor, an admission that the rap world agreed with in full.

Childish Gambino, ‘Because the Internet’

In a particularly weak year (2014) in the Best Rap Album category, Eminem would top the likes of Wiz Khalifa (Blacc Hollywood), Schoolboy Q (Oxymoron) and Common (Nobody’s Smiling) with The Marshall Mathers LP 2, his eighth studio album and fifth overall album to win the trophy. But to those in the know, Childish Gambino’s Because the Internet, the most unsung of the albums in the running, was the true crown jewel and the better album out of the pack for all intents and purposes.