Dissecting rap’s masochistic relationship with the Grammys

In this week’s Rap Column, Vivian Medithi examines how “Music’s Biggest Night” has dealt with hip-hop over the decades.

November 16, 2023
Dissecting rap’s masochistic relationship with the Grammys Will Smith. Photo by MATT CAMPBELL/AFP via Getty Images  

I have at least two fond memories involving the Grammys. The first is thanks to my dad, who routinely purchased the officially licensed CD of Grammy nominees most years in the 2000s. In late 2008, the CD of 2009’s nominees included “House of Cards”, an introduction to Radiohead that left me lovestruck. The second was watching a totally-pregnant M.I.A. perform “Swagga Like Us” with Lil Wayne, Kanye West, Jay-Z, and T.I at the 2009 award ceremony. She went into labor that same night.

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2009 was also pretty special for the Grammys: they actually got rap right. Lil Wayne all but swept the field, taking Best Rap Song (“Lollipop”), Best Rap Album (Tha Carter III), and Best Rap Solo Performance (“A Milli”), with an appearance on the Best Rap Performance by a Duo or Group (“Swagga”); for the Best Rap/Sung Collaboration, his T-Pain collab “Got Money” understandably lost to Estelle and Kanye’s “American Boy.”

Conventional wisdom dictates that the Grammys are doomed when it comes to rap, but hip-hop fans keep tuning in. It’s tempting to chalk this up as a particularly masochistic iteration of Stockholm Syndrome, word to Charlie Brown. But the hope isn’t totally misplaced — the Grammys can and do get things right, and I don’t just mean “picking the nominee I personally like best.”

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In “good” years, the logic for picking X over Y for Best Rap Album feels pretty clear cut, even when the academy skews towards commercial success over artistic merit. Eminem’s Relapse winning Best Rap Album over Mos Def’s The Ecstatic in 2010 doesn’t reflect my personal hierarchy, but it’s hard to argue with Em’s run of 2009 singles.

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But those good years are hard to appreciate when the bad years are so egregious: the 2024 Grammys will mark 10 years since Macklemore’s infamous sweep at the 2014 ceremony, winning Best Rap Album over Yeezus, Good Kid, M.A.A.D. City, Nothing Was The Same, and Magna Carter Holy Grail. And despite — or more frighteningly, because of — a number of democratic overhauls to the awards’ nomination and balloting processes, this year’s nominees are fairly insipid.

The Grammys have had a contentious relationship with rap pretty much forever. When the Best Rap Performance category was introduced in 1989, some nominees (including Salt-N-Pepa and eventual winners DJ Jazzy Jeff and The Fresh Prince) chose to boycott because the award would not be part of the televised ceremony. The next year, “Bust A Move” beat out “Fight The Power” by Public Enemy and De La Soul’s “Me Myself and I,” cementing the awards’ reputation as a middlebrow trophy for consumer-oriented hip-hop.

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The 2000s didn’t break from the awards’ commercial posture, but the sheer number of popular rap albums meant the Recording Academy was far less likely to embarrass themselves — it’s hard to be upset that The Blueprint and Get Rich or Die Trying didn’t notch wins in 2002 and 2004 when they both lost to Outkast. But this points to the central issue with the Grammys: outcomes are hyper-dependent on the nominees’ name recognition and crossover appeal.

You don’t have to take my word for it. Here’s VIBE founding editor Rob Kenner writing about his experience as a Grammy screener for Complex in 2014:

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I soon learned another unwritten rule during private conversations with other committee members: be careful about green-lighting an album by someone who was really famous if you don’t want to see that album win a Grammy. Because famous people tend to get more votes from clueless Academy members, regardless of the quality of their work. This is especially true in specialized categories like reggae and, to a lesser extent, hip-hop, where many voting members of the Recording Academy (who tend to skew older than the demographic for rap music) may not be well acquainted with the best releases in any given year.

This drives back to the Grammys’ voting process. The Academy receives submissions for the awards through the end of the eligibility period, either from artists themselves or a member of their label or PR. These submissions are divided into genre categories by screening committees that determine whether an album is at least 51% pop or rap or R&B, and therefore eligible for an award in that category. The entire list is released to roughly 12,000 dues-paying ($100/year) Recording Academy voting members who vote for a limited set of awards across different “fields” (genres) to select nominees. After those votes are tallied, the nominees are sent out for a final round of voting.

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This is a pretty reasonable set-up: let the self-professed genre experts pick the top 5 and then a bigger pool of interested parties chooses the best of the bunch. Ideally, the winner has genre bonafides (determined by the screening committee), artistic merit (vetted in the nomination process), and popular appeal (confirmed by the final vote).

In practice, results can vary for a number of reasons. First and foremost, rap’s reduced presence in Recording Academy membership, a problem CEO Harvey Mason Jr. freely admits. “Rather than waiting for people to ask to join, we’ve made a conscious effort to reach into different genres of music to say we need more of X or Y,” Mason Jr. told Rolling Stone last month. “We also wanted to increase our Black membership. Compared to the industry, we’re fairly underrepresented in the Black music genres.”

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The Grammys have also cracked down on less-informed voting, recertifying members in recent years to ensure they remain qualified to vote as peers of the nominees, and narrowing the number of votes members can cast for nominees and awards to just 10 categories across three fields, plus the six awards in the “general” field. In previous years, members could vote in a wider range of awards and fields — the year Macklemore won, members could vote in up to 9/31 fields for nominations and as many as 24/31 for the awards themselves.

The biggest change to the Grammys process came in April 2021, when the Academy announced it would be dissolving its nominations review committees. Initially established in the mid-'90s, these opaque committees could massage and adjust the nominee list before final voting; in a 2020 complaint by ex-CEO Deborah Dugan, these same committees were said to be “regularly swayed by the Grammys board, who push nominations for artists who they either want to perform at the ceremony, have relationships with, or both.”

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[NOTE: Less pertinent to the voting process, but more crucial to the Academy’s reputation, was that same complaint’s allegation that Dugan’s predecessor, Neil Portnow, was fired not for misogynistic comments about female artists, but for raping a female member of the Recording Academy. While Dugan and the Academy settled her complaint out of court, the allegations against Portnow have resurfaced following a Jane Doe lawsuit this past week.]

Even following these changes, the recent history of rap Grammys isn’t exactly reassuring. Best Rap Album wins for Tyler, the Creator and Kendrick Lamar were deserved, but not necessarily out of character — both had won the same award once or twice before under previous voting structures. Still, the tilt towards populism has been beneficial in other respects, i.e., netting Future his second Grammy and first as a lead artist (“King’s Dead” with Jay Rock and K Dot won Best Rap Performance by a Duo/Group in 2019).

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But maybe that’s the biggest issue of all with the Grammys and hip-hop. If Future couldn’t get an album recognized until 2023; if 50 Cent only got one for featuring on “Crack a Bottle;” if 2Pac and Biggie don’t have Grammys: who cares about these awards anyway? Winning or performing boosts sales, but the rappers capable of garnering nominations from the Academy are already fairly well-established; it’s probably more lucrative to get your name in a larger font on the Rolling Loud flier.

I’ll never blame artists for wanting validation from their industry peers. And perhaps as younger and more diverse artists join the Academy, the awards too will become sharper and more interesting, both in nominations and recipients (I won’t hold my breath, but I would like to see it). Still, no matter how corny the Grammys get, I can’t quite bring myself to pretend they don’t matter — how else could they make so many people miserable all at once?

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Rap Column is a column about rap music by Vivian Medithi and Nadine Smith for The FADER.

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Dissecting rap’s masochistic relationship with the Grammys