Top 15 Times The Grammys Did Hip-Hop Dirty

15. ODB Sets The Precedent

The year was 1998, and White People had a strange fascination with mopey women singing depressing songs. We showed our appreciation for this vanilla brand of Menstrual Rock by awarding Shawn Colvin (who?) the Song of the Year Grammy…and Wu-Tang Clan’s Clown Prince showed his appreciation for the children when he bum-rushed the stage, paving the way for 50 Cent and, of course, Kanye West to do the same in the years to come. For the record, at the time, Big Baby Jesus was absolutely excoriated for his “stunt,” because the poor little white woman didn’t get her chance to shine…sound familiar, Kanye?

14. Young MC Beats Public Enemy

On its own, Young MC’s “Bust A Move” is a pretty decent song. But in terms of “classic Hip-Hop from the golden era,” Public Enemy’s “Fight the Power” is in a class all its own. In 1989, both songs were up for a Grammy — namely, the Grammy for Best Rap Performance. You wanna take a wild guess as to which song took home the trophy?

13. Robert Plant & Allison Krauss Trump Lil’Wayne & Young Money

Let’s start by establishing the following: as the lead singer of Led Zeppelin, Robert Plant is in rarefied air. His voice is credited as one of the pillars upon which heavy metal was founded, and in the rock pantheon, he is revered as all but a God. With that said: his duet album with Allison Krauss was, especially in hindsight, a schlocky mess. Yet, somehow, it was nominated for Album of the Year…the same year that Lil’Wayne’s Tha Carter 3 was up for the same award. (As a refresher: Tha Carter 3 had “A Milli,” “Lollipop,” “Mrs. Officer,” and “You Ain’t Got Nothin’.”) Do we even need to tell you which album took home the award?

12. Outkast Loses to O Brother Where Art Thou

In 2002, Outkast dropped Stankonia, a now-classic album that featured all original compositions from the Atlanta duo. That same year, T-Bone Burnett put together a bunch of songs from the 1930’s, threw it onto a soundtrack for the (admittedly good) movie O Brother Where Art Thou, and called it a day. Both albums were up for a Grammy. Guess what happened next. Go ahead, GUESS!

11. Jay-Z & Linkin Park’s Collaboration Takes Home a Grammy

Never mind the implication that the only time rap is worthy of bringing home a prize is if they make it milquetoast (because God forbid the white folks get offended)…this collaboration was just…so…wrong. I really wish that Hip-Hop folks would consult with rock folks before deciding to collaborate with artists — we’re all-too-happy to steer you in the right direction so you don’t look silly in hindsight. (Collaborating with Paul McCartney? Yes. Collaborating with Linkin Park? NO!)

10. The Lonely Island Makes Fun of Rap, Gets Nominated for a Rap Grammy

In 2010, The Lonely Island (a pair of white guys so “edgy,” they made Malibu’s Most Wanted look like Straight Outta Compton) enlisted T-Pain to do a featured verse for their song “I’m On A Boat.” As a reminder, “I’m On A Boat” made fun of Hip-Hop. The entire song was a Weird Al-esque trip into poking fun at Hip-Hop stereotypes. And for their efforts in making fun of Hip-Hop, they got nominated for a Hip-Hop Grammy. Amazingly…they lost (to “Run This Town”).

9. Steely Dan Trounces Eminem

Proving, once again, that the Grammy voting committee is run by old white men who probably use the words “whipper snapper” in everyday conversation and think that telling a black man that “he speaks so well” is a compliment, the committee thought that 2000’s Album of the Year belonged, not to The Marshall Mathers LP (the album that gave us “Stan,” “The Way I Am,” “The Real Slim Shady,” “Kim”…you know, all the songs that ‘heads quote as the songs that made Eminem, well, Eminem…), but to Steely Dan’s Two Against Nature that featured such delightfully wholesome songs as “Gaslighting Abbie.” Because, you know, singing about mentally abusing the sh*t out of your girlfriend is preferable to rapping about beating the sh*t out of your girlfriend…

8. Arcade Fire Trounces Eminem

You would have thought, eleven years later, that the Grammy voting committee would have caught on about Eminem kinda-sorta being a big deal…and you would be wrong. In 2011, Eminem dropped Recovery. That same year, Arcade Fire (I know, who?) dropped The Suburbs, a purportedly “rock” album that was anything but (because, frankly, they’re Canadian). Both go up for a Grammy. You know what happens next…

7. Bon Iver Bests Nicki Minaj

Whatever your opinion about the Pink Friday rapper, Nicki Minaj is a modern cultural icon, much like Madonna before her. In 2012, the Grammy committee finally sat up and took notice of the girl Hip-Hop has loved since the Mixtape Nicki days, and gave her a shot of winning the Best New Artist Grammy. She lost to Bon Iver (WHO?!)…an upset so strange and cringe-worthy, even Bon Iver had to admit that it was “hard to accept this award.”

6. Macklemore Bests Drake & Kendrick Lamar

Rather than go into extensive detail about cultural appropriation, White Privilege, and the gobsmacking WTFery of the Grammy committee, I’ll just leave this song here and remind you that THIS won a Grammy.

5. Puffy Beats Biggie

In this case, the upset had to do with the fact that Puffy’s No Way Out album somehow was superior to The Notorious B.I.G.’s Life After Death classic swan song. As a producer, businessman, and entrepreneur, Puffy is second-to-none. As a rapper, however, Puffy leaves much to be desired. Too bad the Grammy committee disagreed…

4. Tupac What? Biggie Who? Coolio!

Like The Beatles and The Rolling Stones are rock gods, Tupac and Biggie are rap gods. Now, while Coolio certainly has earned his place in Hip-Hop history — to be fair to all involved, his Gangsta’s Paradise album was only the second Hip-Hop song in Grammy history to get nominated for Record of the Year — it leaves a weird taste in the mouth when you realize that the same year that “Gangsta’s Paradise” took home the trophy, “Dear Mama” (by Tupac) and “Big Poppa” (by Biggie) were denied the same award.

3. Tony Bennett Beats Out Three Other Rap Demigods

Nas’ Illmatic, Biggie’s Ready to Die, and Outkast’s Southernplayalisticadillacmuzik all go up for a Grammy. Who wins? If you guessed Tony Bennett’s MTV Unplugged album, congratulations! You win a cookie!

2. Celine Dion Trumps The Fugees

Celine Dion. God bless her — Canadian, harmless, pipes of steel, Titanic, Vegas residency — she’s doing her thing. You can’t get mad at that. Actually…you can…when you consider that her Falling Into You album trumped The Score. And you can’t say it was because “My Heart Will Go On” was on the album…because it wasn’t. The Grammys made up for it later by giving Lauryn Hill’s solo effort damn near every Grammy ever invented…but that inital BURN was a doozy.

1. The Golden Age of Hip-Hop Gets A Grammy Slapdown

The year was 1988. And in this day and age, where everything is auto-ingestive and Auto-Tuned to death, it’s hard to appreciate that this was the year of the following albums and songs: 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.”

That lineup alone was enough to galvanize Hip-Hop into the pop culture zeitgeist.

And how did the Grammys celebrate this in 1988?

By awarding the Best Rap Performance trophy to this song:

I mean…FAM.

Bernadette Giacomazzo invites you to talk to her on her website, www.bernadettegiacomazzo.com, and on her Twitter at @berngiacomazzo.