Kanye West's Most Random Moments

By Paul Cantor

Kanye’s new stylist and life coach is Cassius Marcellus Cornelius Clay, a 20-year old aristocratic Yale student with a keen eye for designer clothes and serious ties to old money. Like, really old money. Okay, let’s join in together now and let out a collective “WTF?” Aaaaand we’re back.

Apparently Kanye met Clay this past summer as they were both shopping in Barney’s, in New York. Ye’ got to admiring his footwear, they talk, exchange info, and stay in touch. Clay soon becomes a part of Mr. West’s inner circle, helping him with key decisions, like what to wear, and more importantly, his twitter apology to Taylor Swift. By the end of the summer, he reportedly asks the blue blood to drop out of Yale and join his team full time.

If the move comes off as random, it’s really anything but. For Kanye, it actually falls in line with a whole host of other things he’s done in his career and personal life that have made very little sense to those within the often constrictive urban music world. Let’s take a trip down memory lane and explore Kanye’s top random moments.

1. Signing Fonzworth Bentley to G.O.O.D. Music

Kanye’s always had a thing for guys with a patrician edge, which somewhat explains him signing Diddy’s former valet/personal assistant Bentley to his boutique record label in the mid-aughts. This, despite the fact that hip-hop fans knew Bentley more for his flare with an umbrella than a microphone. After his rap career failed to launch (In 2008, he released a single and video for “Everybody,” featuring Ye’ and Andre 3000, but it didn’t catch on) he starred in his own VH1 reality show, “From G’s to Gents,” where he was part life coach, part stylist to a bunch of social misfits. Sound familiar?

2. Following Exactly One Person on Twitter

Before his short dalliance with following Taylor Swift and Justin Bieber on Twitter, Ye’ only followed Steven Holmes. Who? Exactly. It’s unclear as to why Kanye ever really decided to follow Mr. Holmes, but the Nottingham University media student didn’t care anyway. “I just commented on something on Kanye West’s account and next thing I know he’s following me,” he told the Coventry Telegraph. "The funny thing is I like his music but I’m not his biggest fan. Fame has never appealed to me. It's vacuous.” Ye’ wasn’t too pleased with Stevie’s attitude, and surprise surprise, he soon unfollowed him.

3. "Dating" with Amber Rose

Mr. West has a thing for plucking people from obscurity and watching them become famous by association. Enter Amber Rose. One day she appeared on his arm and the next she was fodder for endless gossip. Prior to ‘Ye, Rose was reportedly a friend of Rihanna and had done scant modeling while appearing in the occasional rap video. To West though, she was like a personal Brigitte Nielsen, this statuesque goddess-type with the fashion sense to match. She is, to-date, perhaps West’s best fashion accessory.

4. Jon Brion is my Co-Pilot, er, Co-Producer

Most artists have trouble topping themselves after selling one million copies of their debut album like Kanye did with College Dropout. Kanye, however, beat the odds. Impressed by his work on the film score for Eternal Sunshine of the Spotless Mind, he hired multi-instrumentalist Jon Brion to help compose the myriad layers of sound that would make up his cinematic second LP, Late Registration in 2005. The result was a heavily-orchestrated affair, complete with lush arrangements and chamber-style instrumentation that upped the ante on what the Louis Vuitton Don was artistically capable of delivering.

5. ‘Ye Goes Electro

For a guy who rose to fame speeding up classic soul records, nothing drew a bigger side eye from the overly critical hip-hop crowd than sampling Daft Punk for the first single from his 2007 LP Graduation. His first single “Stronger” borrowed from the quirky French duo’s 2001 single “Harder, Better, Faster, Stronger” and capped off an album that was heavy on synthesizer stabs and “four on the floor” drum beats. It was a stylistic shift that changed the landscape of urban pop, opening up the airwaves for a rush of Euro-inspired hip-hop dance music. Black Eyed Peas fans the world over rejoiced.

6. 808s and Heartbreak

Perhaps Kanye’s biggest WTF moment was his choice to sing an entire album’s worth of material in autotune. Still reeling from the death of his mother Donda West in 2007 and the dissolution of his relationship with then-fiancee Alexis Phifer, ‘Ye hit the lab and produced his most random work to-date. 808s is a big sounding album full of subdued sadness. It’s a far cry from “Touch The Sky” and “Through The Wire,” which were uplifting songs that were both inspirational and motivational. All of a sudden the little engine that could, couldn’t, and it kind of hurt hearing it.

7. “Portrait of Power” for “Power”

Video girls and Ciroc is child’s play. At least that’s what Kanye seemed to say when he commissioned visual artist Marco Brambilla to direct his “Power” video, which was more of a painting with moving parts than a rap video at all. Inspired by Brambilla’s “Civilization” video installation, Kanye had the artist do something similar with “Power.” Someone get Hype Williams on the phone.

8. Miri Ben-Ari Rocks The College Dropout

Does anyone remember Miri Ben-Ari “the hip-hop violinist”? Probably not. But before he could afford to hire someone like Jon Brion, Kanye had to rely on Ms. Ben-Ari to add the symphonic elements to his first LP, College Dropout. The random pairing found the Israeli-born Ben-Ari playing the violin all over that project and even toured with the rapper in 2004. She also received a Grammy for her violin arrangements on “Jesus Walks,” which is kind of ironic, considering her Jewish background.

9. “George Bush Doesn’t Care About Black People”

In 2005, during an NBC telecast of a concert to support the victims of Hurricane Katrina, Kanye uttered the aforementioned famous words. It was a completely unexpected moment, with West deviating from the script prepared for him and co-presenter Mike Myers. Perhaps this was just his warm-up act though, as later years have found have found him... somewhat infamous for saying outlandish ish on more public stages.

10. Directing Drake’s “Best I Ever Had” Video

When Drake stepped on the scene, the Canadian-bred actor-turnt-rapper was essentially Kanye lite. A branch from the tree that birthed 808s and Heartbreak, Drizzy was all conflicted sing-songy weeping mixed with random bouts of hip-hop bravado. But when he linked with Kanye and hired 'Ye to direct the video for “Best I Ever Had,” the collaboration was little more than a creative fail. The video masked itself in metaphor, but really trafficked in ass, ass and more ass. It left people scratching their heads as to how two lauded creatives could hatch something so... generic. It was like Kanye went from genius to jerkoff in three and a half minutes. But hey, let’s have a toast!

What's your favorite random Kanye moment? Tell us in a comment below or @MTVRapFix!