Gangsta’s Parodist: Revisiting ‘Weird Al’ vs. Coolio

Fools be in the bars unadvanced with a switch

Uppercuts and fight kicks with Weird Al Yankovic

-Coolio, “Throwdown 2000”

On a scale of pop music beefs from the last 25 years, Weird Al Yankovich v. Coolio would likely fall somewhere in the neighborhood of Morissette v. Coulier and Arrested Development v. Arrested Development. Which is to say, it wasn’t much of a beef at all. To even label it a beef almost seems like an insult to the whole concept of beefs.

And yet, in the time it took for the two to formally and publicly reconcile their differences, The United States has seen 3 presidential elections, 4 new Supreme Court justices, and 20 Now That’s What I Call Music! albums.

On the surface, “Weird Al” and Coolio would appear to be polar opposites, but it’s striking how similar the two are, artistically and personally. Each were born and raised in Southern California (Coolio is Compton-bred, Yankovic Straight Outta Linwood) where as children, their bookwormish penchants found them ostracized socially. To find solace, they turned to music, where they rose to prominence by offering self-effacing, endearingly agitating alternatives to the increasingly self-serious musical genres of West Coast Gangsta Rap and modern pop.

Their paths eventually intertwined on January 28th, 1996, at the American Music Awards. A few weeks after Billboard certified “Gangsta’s Paradise” the number one single of 1995, Coolio took home the AMA for “Favorite Rap/Hip Hop Artist” and joined Yankovic — sporting his own Coolio-inspired vertically deadlocked look — as a presenter.

Judging from the footage, they appeared congenial, even fraternal, as they announced Pearl Jam as the winner for Favorite Alternative Artist. If Coolio had any feelings of animosity toward Yankovic stemming from the parody, he hid it well.

But things would change only a month later, on February 28th, at the Grammy Awards, where Coolio impressively edged out the likes of Biggie’s “Big Poppa” and 2Pac’s “Dear Mama” to take home the Grammy for Best Solo Rap Performance

It was here, backstage, that the dispute first manifested itself. When asked by a reporter as to whether or not he’s heard Yankovic’s parody, Coolio confirmed that he had, but did not approve:

I ain’t with that…I think that my song was too serious…I really…don’t appreciate him desecrating the song like that… his record company asked for my permission, and I said no. But they did it anyway…

A few days later, a befuddled Yankovic attempted to diffuse the spat by issuing a formal explanation of his position via email:

…two separate people from my label told me that they had personally talked to Coolio… and that he told them that he was okay with the whole parody idea…Halfway into production, my record label told me that Coolio’s management had a problem with the parody, even though Coolio personally was okay with it. My label told me… they would iron things out — so I proceeded with the recording and finished the album.

Cooler heads seemingly prevailed until a year and a half later, with the release of Coolio’s My Soul. The 11th track of the Gangsta’s Paradise follow-up, “Throwdown 2000”, directly references Yankovic, and as such, was identified as the latest salvo in the presumed-dead battle. But the referencing line, found at the top of this article, is so tepid and toothless that it could hardly be classified a diss lyric, let alone a diss track, and goes largely ignored by most, including Weird Al.

The next mention of the dispute came two years after the release of My Soul, and courtesy of Yankovic, by way of the “Weird Al” episode of VH1’s Behind The Music. In it, the parodist claims he sent a sincere letter of apology to the rapper, but had yet to receive a response, which doesn’t come until August of 2000, on the syndicated radio show LoveLine, when Coolio professed to have forgotten about the squabble entirely, saying:

That’s an old subject, ya know, basically I don’t even think about it anymore, I don’t care, ya know. Much peace to Weird Al’s family.

Though he would receive partial royalty checks, Coolio never sought legal recourse. More than half a decade passed before a formal reconciliation occurred during an impromptu reunion at the XM Satellite booth at the 2006 Consumer Electronics Show in Las Vegas. Later, when asked later to explain the his mindset at the time of the seemingly chance encounter, Yankovic replied:

>…I dont remember what we said to each other exactly, but it was all very friendly and after a minute, he was gone. I turned to the next person in line and said, Did that really just happen?

Coolio would go on to score a few more modest hits — though none reached the chart heights of “Gangsta’s Paradise” — and would later find a career resurgence as celebrity reality TV fixture in the States and abroad.

Conversely, the years have been much more kind to Yankovic, who recently released his most recent tour DVD “Weird Al Yankovic Live: The Alpocalypse Tour” and has shown no signs of slowing down anytime soon.

That he has enjoyed something of a career renaissance since the advent and explosion of Internet comedy should come as a surprise to few. It could be argued that his most lasting and indelible mark on music, comedy, and popular culture as a whole, has been in giving a voice of an entire generation of nerds, geeks, weirdos, and dweebs, who were previously voiceless. He made making fun of the cool kids cool, a notion highlighted by a decade long stand-off with a guy so cool he was actually named “Coolio.” Yankovic he never backed down and stood firm. It seems, in this case, the weird kid won.

Special thanks to the uber informative “Weird Al” fan site We’ve Got It All On UHF.

Conor McKeon is a Webby-Honored writer/editor living in Brooklyn. In addition to being a former CollegeHumor staff writer, he has contributed to The Onion, Yankee Pot Roast, Mental_Floss, and He tweets here and blogs here.

Gangsta’s Parodist: Revisiting ‘Weird Al’ vs. Coolio