The Grammys' Biggest Hip-Hop Mistakes: Snubs, Errors, and Embarrassments

The second rap song ever nominated for Record of the Year was Coolio's "Gangsta's Paradise," at the 1996 Grammys. It's a pretty catchy song, and has some memorable lyrics, even if Coolio isn't the most charismatic MC to grace the stage (That hair, though). The nod seems reasonable enough, until you realize that 2Pac and the Notorious B.I.G. were both denied awards that very year (for "Dear Mama" and "Big Poppa," respectively). Even Skee Lo's "I Wish" aged a little better than the Coolio classic. That's saying something.

Hip-hop completely redefined the role of the producer in music history. Sure, a few producers (Quincy Jones, Phil Spector) became a kind of household name prior to the rise of hip-hop, but hip-hop gave producers a central role. Since that time, though, only Dr. Dre and the Neptunes have managed to win Producer of the Year honors (Rick Rubin's also won, but not for hip-hop releases). One particular snub? Timbaland. In 2001, he was in his prime. After crossing over from R&B to hip-hop, he made a permanent mark in the history books, releasing charting single after charting single, and making beats for Missy Elliott, Jay-Z, Fabolous, Bubba Sparxxx, Jadakiss, the Ruff Ryders, Petey Pablo, Ludacris, and Lil Kim, to name a few. But he lost that year to T-Bone Burnett, the producer of the O Brother Where Art Thou? soundtrack, memorable only to people who still buy CDs at Starbucks.

We get it: old people run the world (or at least the Grammy nomination process). And Tony Bennett is a legend in the game, the best of the Italian-American pop crooners since Sinatra passed away. His appearance on MTV's Unplugged was an attempt, at some level, to increase, uh, intergenerational understanding, or something. But rather than forcing older artists on your kids, it might have been better to acknowledge that the kids were coming up with some music of their own. The same year Tony Bennett won his Grammy, three hip-hop debuts dropped that went on to drastically change the genre: Illmatic, Ready to Die and Southernplayalisticadillacmuzik announced the arrivals of just a few of the names that would go on to define the genre (and only a year after Doggystyle and Enter the 36 Chambers). It was an epic time in hip-hop history, and as usual, the establishment preached understanding while practicing the opposite.

Nas reportedly has 18 Grammy nominations under his belt (he talked about it on Angie Martinez earlier this year). Not one win. His first was in 1997: Best Rap Solo Performance for "If I Ruled The World." Instead, LL Cool J won for "Hey Lover." It seemed like Nas couldn't catch a break. It happened again in 2000, 2003, 2008, 2009, 2010 and now he's up for four in 2013 for tracks from (and the album itself) Life is Good. At some point, he has to win, right?

The Lonely Island's "I'm On A Boat" was nominated for Best Rap/Sung Collab in 2010. Reminder: It's a satirical track, featuring T-Pain, that made fun of rap and the artists that, inevitably, it was nominated with for the Grammy. Originally a Saturday Night Live digital short, "I'm On A Boat" was the first comedic track of an album that wasn't placed in the Best Comedy Album category. It was a spoof: the video, the lyrics, the demeanor. Although it went platinum, it lost to Jay-Z, Kanye West and Rihanna's "Run This Town." Still, it's like Weird Al being nominated next to Bruce Springsteen: Any other genre, this would never happen. The Grammys literally sometimes treat hip-hop like a joke.

Ol' Dirty Bastard stormed the stage at the Grammy's during Shawn Colvin's acceptance speech to protest losing his award to Puff Daddy, but honestly, No Way Out is a pretty incredible album. It has an epic scope, well-(ghost)written lyrics, classic singles and an overarching aesthetic instrumental in transforming hip-hop into the all-encompassing Billboard-conquering monster it became for the next several years. But it's also not as good as Life After Death. Puffy had personality, ambition and vision, but as a rapper, he never had the style, the presence or the swagger Biggie brought to the table. The Grammy committee disagreed.

Sure, there were plenty of rap songs that probably deserved a Best Rap Solo Performance award at the 1997 Grammy's over "Gettin Jiggy With It," but not that many. And who could resist Will Smith spitting commercial-peak Nas bars over a Sister Sledge loop? Big Willy Style indeed. The following year, though? Come on, son. Nothing about "Men in Black" was cool. It did flip a dope Patrice Rushen track, but switching up the hook from "Send me forget-me-nots / to help me to remember" to "Here come the Men in Black / Galaxy defenders" is beyond corny. Movie tie-in raps, with lyrics about your action film character, aren't cool. Neither is rapping as a character who is also being sold as toys at a fast food chain. But surely, you think, the crass commercialization of hip-hop is as American as apple pie; perhaps this was just a weak year for hip-hop. Without even going beyond the list of nominees for 1998: "Put Your Hands Where My Eyes Can See"? "The Rain (Supa Dupa Fly)"? "Hypnotize"?

Regardless of what your favorite Outkast record is, Stankonia is a great fucking album. You know why it's great? The same reason all of Outkast's music is great: because it's so original. So lo and behold the irony that they lost for Best Album to a record that featured no original compositions. The O Brother soundtrack is impressive, sure, because T. Bone Burnett holds it down and the Coen Brothers made the music from the soundtrack a major part of the film, but this is yet another classic example of the Grammys looking backwards instead of looking forward. Like, 1930s-revivalist, backward.

In 2003, 50 Cent wasn't just a rap phenomenon, he was a pop culture force, full stop. He was a certified hit-maker who had sold a gazillion records and he was already a rap legend. The Best New Artist award was his to lose and of course, he lost it. 50 protested his loss by making a cameo on stage during Evanescence's speech. We're not saying 50 should have won just because he sold a shitload of records (admittedly, Evanescence did too) but because he's one of the most significant rappers of the 2000s and Evanescence is...an early-aughts post-nu-metal Creed fronted by a woman.

In 2005, the Black Eyed Peas won for "Let's Get It Started," a pop-rap radio banger, for sure. But that was over Beastie Boys' "Ch-Check It Out," Snoop Dogg and Pharrell's "Drop It Like It's Hot," Terror Squad's "Lean Back" and The Roots' "Don't Say Nuthin'." Yes, out of those fantastic nominees, the BEP nailed it. And then, in 2006, "Don't Phunk With My Heart" landed them the same award-instead of Common's "The Corner," Eminem, Dre, and 50 Cent's "Encore," Ying Yang Twins' "Wait (The Whisper Song)" but none more surprising than The Game and 50 Cent's "Hate It or Love It." Come on, Grammys. Two years in a row, and even five years later it's hard to really decipher any differences between the Black Eyed Peas songs, no more so than when they're winning Grammys.

Kanye West got a reputation for being a bit of a sore loser at the Grammys, but at a certain point, it was hard to say it was unfounded. He lost Album of the Year three times in a row for his first three records, and each time, it was to artist who peaked creatively decades early. No disrespect intended to Ray Charles, an American icon and musical legend, but his late-period A&R'd-to-death Genius Loves Company is not a record on par with The College Dropout. Nor is U2's How to Dismantle an Atomic Bomb a bad record, but the band's creative peak was in the 1980s and 1990s; by 2006, Late Registration deserved to run the board. Perhaps the strangest of all was when jazz pianist Herbie Hancock—an incredible artist whose most celebrated work was released 40 years earlier—snagged Album of the Year over not just Kanye's biggest crossover smash Graduation, but Amy Winehouse's indelible Back to Black as well. Then, the 2011 Grammy Awards snubbed West's My Beautiful Dark Twisted Fantasy from the Album of the Year category entirely, to the surprise of onlookers everywhere.

Lil Wayne made an unlikely emergence from the shadows of The Hot Boys and Cash Money to become the biggest rap star of the '00s this side of 50 Cent. Few rappers have managed such universal acclaim: respected by 'heads, celebrated by the streets, exhaulted by skateboarders and beloved by pop fans, he is one of the genre's most respected figures. The Carter III was, from a commercial perspective, his crowning achievement. But wait: a duet album from a bluegrass singer and Led Zeppelin's vocalist made a record together. And doesn't that combination sound just a little bit more palatable to listeners of a certain age? Apparently the Grammy committee thought so as well, and Weezy was denied his big shot at the award.

Celine Dion has had 21 Grammy nominations and 5 wins, and in 1997, she took Album of the Year for Falling into You. It was only her fourth English-language album-but her 21st overall. Yes, 21. Meanwhile, The Fugees disbanded in 1997 but first, won the Best Rap Album for The Score and "Killing Me Softly" for Best R&B Vocal Performance. But lost to Dion for Album of the Year. Couldn't she have just let them win? It was their second and last album, ever. Plus we can name nearly every song on The Score and no, "My Heart Will Go On" wasn't on Falling Into You. Nice try.

It was bad enough that it took the Grammy Awards until 1989 to even give hip-hop its own category; even then, though, the year that brought us certified hip-hop classics The Great Adventures of Slick Rick, It Takes a Nation of Millions and Straight Outta Compton got snubbed. Why? Because the awards show didn't even institute a separate album award until 1996, missing a run of some of the genre's most consistent, adventurous and ground-breaking work. At the time, there was a running belief that hip-hop was a 'singles genre.' While there are certain periods in the genre's history where this is unquestionably the case, the period during which the Grammys decided hip-hop was worth paying attention to was not one of them.

"Feel Me Flow" is a crazy song, no doubt. And, compared with their popularity in their heyday, Naughty By Nature probably don't get the respect they deserve-Treach could be a monster on the microphone. But seriously? Everyone on the Grammy committee votes in each category, so many times, genre specialists are overwhelmed by the votes of genre dilettantes, which may explain things to a degree. But just for perspective, a quick rundown of rap albums released that same year (nominees in bold): Me Against the World, E 1999 Eternal, Return to the 36 Chambers: The Dirty Version Only Built for Cuban Linx, The Infamous, Liquid Swords, Coast II Coast, Soul Food, On Top of the World, Dogg Food, Safe + Sound, True, Dah Shinin, In a Major Way. Also receiving a nomination for the 1996 Grammy Awards: Skee Lo's I Wish LP.

Arrested Development had some cool singles. They also had to take the unfair weight of standing in for everything that was "okay" about hip-hop to critics of the time. This was the year of The Chronic, a moment of radical change for the genre and an increasing diversification of styles. Gangster rap was the emergent form throughout the United States. There was a problematic aspect to gangsta rap's ascension, no doubt. But critics who rallied around Arrested Development (the group also won Best New Artist) found themselves feeling a little foolish when the group's follow-up was universally panned, and the world seemed less responsive to the message they preached.

Groups and duos have been a part of hip-hop throughout its history, but it wasn't until Quincy Jones came along to add his paternal legitimacy to the genre that it could earn a Grammy. "Back on the Block" had a pretty impressive lineup, but as a song, it just feels wrong to hear Ice T rap about his homies getting killed over cheery pop-dance production. It was evident from a production standpoint that Q wasn't adapting to hip-hop quite as smoothly as he had to disco. "Back on the Block"'s christening of the Best Rap Song by a Duo or Group category was even more galling when you realize what it beat out: "The Humpty Dance," by any measure a classic hip-hop single and genuinely-fun party song, which was likely heard back on a few more blocks.

First thing's first, we're not messing with the worst; Young MC's "Bust a Move" is a classic pop-rap single, and certainly deserves a place in the pantheon of classic cuts from hip-hop's golden era. But still: this was hip-hop's golden era! OK, sure, nominees like DJ Jazzy Jeff & The Fresh Prince's "I Think I Can Beat Mike Tyson" and Tone Loc's "Funky Cold Medina" would have a tough time topping "Bust a Move," but "Fight the Power" is in rarefied air, one of the truly titanic hip-hop singles in history. De La Soul's "Me Myself and I" (never mind "Eye Know," which did not receive a nomination) are similarly celebrated records. Sure, "trivial" pop rap can often receive short shrift from critics looking back on the moment today. But at the time, it definitely felt as if the Grammy Awards were giving short shrift to the genre, coming from the opposite direction, by refusing to acknowledge it unless it reached a critical mass of popularity.

It Takes a Nation of Millions to Hold Us Back. Straight Outta Compton. The Great Adventures of Slick Rick. By All Means Necessary. Critical Beatdown. Long Live the Kane. Straight Out the Jungle. Life Is ... Too $hort. Act a Fool. Goin Off. Tougher than Leather. Follow The Leader. Strictly Business. Power. "Talkin All That Jazz." "Top Billin." "The Symphony." "Plug Tunin." "The Vapors." "The 900 Number." "Caught Up (Remix)." "Going Back to Cali." "Road to the Riches." "Posse on Broadway." "Push It." "Supersonic." How was hip-hop's coming-out party celebrated by the Grammy's? A single category ("Best Rap Performance") and a victory for "Parents Just Don't Understand," by DJ Jazzy Jeff and the Fresh Prince. Oh.