Whenever someone says they miss the Old Kanye, a huggable—if forlorn—icon pops to mind. The College Dropout Bear, Kanye West’s early-career mascot, was as intertwined with the artist’s breakout image as the colorful Polos, Louis Vuitton bags and chipmunk-sounding soul samples.

What might have appeared like a goofy gimmick at first sight actually is stuffed with a deeper personal symbolism, as The Dropout Bear’s journey unfolds over the course of West’s strategically planned first three albums. As clever as he was cuddly.

Hip-hop had long established a history of backup dancers and hypemen prior to Kanye's debut of his bear mascot. Early Def Jam act Public Enemy drilled its direct, purposeful mission across with the silent backing of in-step S1Ws, for instance, adding to the imagery and motif.

But never had a superstar burst on the scene supported by the type of character you could imagine handing out lollipops to children at a fair. The Dropout Bear was approachable, so Kanye must be too.

Despite the wishes of his mother, Donda West, an English professor at Chicago State University, Kanye dropped out of university in order to purse his musical dreams full-time. Hence the title of his 2004 debut album, The College Dropout, which celebrates its 16th anniversary on Feb. 10.

The Dropout Bear represents the pursuit of happiness and living life on Kanye's own terms, not by societal standards. He didn't need to go to college to pursue his dreams and the bear offers a similar symbolism of hope for his fans. ’Ye defied the odds and succeeded by taking the ultimate risk: following one's dreams. The College Dropout debuted at No. 2 on the Billboard 200 chart when it was released in 2004, selling 441,000 copies in its first week of sales.

On the rap end, Kanye was defiant because he wasn't fitting into the stereotypical rapper mold at the time. Back then, it was basically be a gangsta rapper or be a conscious rapper. Kanye served as a man in the middle. Using the teddy bear at the peak of gangsta rap was defiant, he used his own unique aesthetic. On the personal end, he defied the standard college course.

“It was drummed into my head that college is the ticket to a good life,” Donda told the Chicago Tribune in 2004, “but some career goals don't require college. For Kanye to make an album called College Dropout, it was more about having the guts to embrace who you are, rather than following the path society has carved out for you.”

Roc-A-Fella Records

The bear mascot, of course, represents the college life Kanye left behind, and the visionary rapper-producer—as ever—was very hands-on when it came to the packaging and promotion of his art. So he had this idea of donning the bear suit for The College Dropout cover art while sitting in collegiate bleachers. Photographer Danny Clinch shot the images, and the LP’s art director, Roc-A-Fella’s go-to in-house designer Eric Duvauchelle, was presented with a binder full of options.

“I quickly gravitated towards him sitting alone on the bleachers in the mascot suit. It was interesting to me as The Dropout Bear is meant to be the most popular representation of a school, yet in the cover, it shows Kanye in the mascot suit/head, all alone sitting on bleachers,” Duvauchelle explained of the cover art.

Although partial to the shot of Kanye holding the bear head, Clinch too was taken aback when Kanye elected for the photo with the bear head on his shoulders, masking his face. “But at this point, knowing his history of breaking the rules,” Clinch added, “it doesn’t surprise me at all.”

Theo Wargo, Getty Images

The scholastic theme extended through The College Dropout’s liner notes, designed in the style of a college yearbook with throwback photos of the project’s contributors, and The Dropout Bear mascot accompanied Kanye onstage during live performances.

That educational motif builds steam in Kanye’s 2005 follow-up, the more sophisticated and ambitious Late Registration album, the cover of which features the wide-eyed Dropout Bear swinging through the school doors, head high, seeking knowledge.

Packaged by Morning Breath Inc., a Brooklyn-based graphic design studio, Late Registration’s photographs were snapped at Princeton University as Kanye’s anthropomorphic teddy sports a letterman jacket, wanders through the lecture halls and goes through stacks of library books. This back-to-school concept was accentuated by the hilarious Broke Phi Broke series of sketches, voiced by comedian DeRay Davis, that spoofs a fictional Black fraternity.

Roc-A-Fella Records

In the third installment of Kanye’s scholastic trilogy, 2007’s Graduation, The Dropout Bear made it, seemingly flying through the air to his next goal in the artwork for the album. A Japanese contemporary cartoon commissioned by one of Kanye’s favorite artists, Takashi Murakami, serves up the album’s beautifully optimistic cover.

The Dropout Bear doffs his graduation cap and is launching skyward, bling around his neck, future bright as he departs an imaginary futuristic metropolis called University City. “The cover is based on Kanye's theme of student life. School. It's a place of dreams, of righteousness, a place to have fun. It's also occasionally a place where you experience the rigid dogma of the human race,” Murakami explained to Entertainment Weekly.

“Kanye's music scrapes sentimentality and aggressiveness together like sandpaper, and he uses his grooves to unleash this tornado that spins with the zeitgeist of the times. I too wanted to be swept up and spun around in that tornado.”

Roc-A-Fella Records

Murakami’s post-modern style, heavily influenced by manga and anime, dominates the LP’s surreal packaging, while West stayed involved in seeing the imagery come to fruition, emailing Murakami visual concepts throughout a creative process that spread over several weeks.

The Graduation album art—crowed one of that year’s five best by Rolling Stone—was brought to Technicolor life via a three-minute music video for the record’s opening track, “Good Morning.” The video, composed by Murakami using fantastic cel-shaded animation, features The Dropout Bear’s panicked rush through University City’s obstacles and concludes with a diplomas and rainbows. It has since been featured in multiple art museums.

While Kanye had originally sketched out an idea for a fourth chapter in The Dropout Bear’s journey—his tentatively titled Good Ass Job LP—Donda’s death in 2007 left the musician devastated and he changed course.

Good Ass Job was ditched in favor of 2008’s 808s & Heartbreak, a fascinating, influential sharp left turn from the Old Kanye and a rather abrupt end to The Dropout Bear as his mascot. Before the stuffed bear’s head was replaced by a repugnant MAGA cap, however, The Dropout Bear made one last tiny came: as a zombified version of his formerly fluffy self on 2010’s My Beautiful Dark Twisted Fantasy.

In a touching story relayed to David Letterman for his Netflix series, My Next Guest Needs No Introduction, 2019, Kanye described his mother giving him a toy bear as a gift just weeks before her death. “I remember my mother bought me a bear that was multi-colored," ’Ye shared. "I was very into Takashi Murakami at that time on that third album, Graduation. So she said it kinda feels like Takashi Murakami, and then I was like, ‘I don’t want that—that ain’t no Takashi Murakami bear.”

Once Donda passed, however, Kanye’s tune changed. He began searching high and low. “I did everything I could to find that bear and I placed that bear on top of all the Takashi Murakami stuff I had in the house,” Kanye said. “But she’s here with us, and she’s guiding us.”

Sixteen years later, The College Dropout Bear has long been stuffed in the closet, a forgotten relic of a wide-eyed era. Fans who grew up on the Old Kanye now feel about The Dropout Bear the way Toy Story's Andy might now feel holding Woody and Buzz Lightyear.

The nostalgia is warm, but times have changed.

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