Born in 1974 and raised in Jersey City, New Jersey, Donnelly spent his high school years skateboarding and writing graffiti—pastimes that inevitably led him to cross the river to New York. According to Donnelly, when he was growing up, graffiti was really the one outlet for young creatives who had an interest in art but limited access. After graduating high school in 1993, Donnelly began experimenting with his trademark “X” and skull and crossbones, rather than just lettering.

Shortly thereafter, Donnelly enrolled at the School of Visual Arts, where he first realized that beyond graffiti, art was a viable career choice. While in school, Donnelly landed a job as an illustrator for Jumbo Pictures, where he contributed background illustration for Doug and (101 Dalmatians*. Working on children’s cartoons was not only fundamental to Donnelly’s aesthetic, it was an eye-opening experience.

In 1996, Donnelly graduated from SVA and took his graffiti to the next level. Managing to procure a key that unlocked the advertising panels of phone booths and bus stands, Donnelly began “subvertising”—subverting advertising by adding his Xs and skulls and fantastical drawings to otherwise bland ads. Fashion advertisements were a frequent target of his, honing on the era’s ubiquitous Calvin Klein and DKNY posters and billboards. While considered vandalism then, today those same subvertisements are considered art in-and-of thsemeselves. “I started to think about it almost like competing with the advertisers for space, [making] work that would last on the streets and almost just be there, but not...Maybe someone doesn’t even stop but later is like, ‘What was that? Weird ad.,’” Donnelly said. Before long, people started to recognize KAWS’ distinct visual language.

Donnelly then turned his focus towards Japan, where contemporaries like Stash and Futura found great success. While some friends lamented—and even mocked—Donnelly’s focus on Japan, his work with the burgeoning streetwear scene helped KAWS become global.

According to Donnelly, no American street artist was making art targeted towards the Japanese market, as “kids weren’t buying art, it just wasn’t on the radar. They’d sooner spend $300 on a pair of sneakers than they would on a small drawing.” So, when Bounty Hunter approached the young artist with a unique proposition—to turn a character into a vinyl toy—it presented the perfect opportunity. For Donnelly, figurines were a substitute for sculpture, an art form that while he was always fond of required either a wealthy patron or significant personal investment and so was out of reach. With the toys, however, Donnelly had the opportunity to transform his 2D sketches to 3D collectibles, while simultaneously creating a product he felt would resonate with Japanese consumers.

The first KAWS character turned into an 8-inch-tall vinyl toy, Companion—a Mickey Mouse-esque character who seemingly just drank from a bottle of poison—was an immediate hit, sold in the best shops of a still nascent subculture that merged art and fashion. Colette, the iconic since shuttered Parisian boutique, was one of Donelly’s first stockists. Building on the success of the Companion, Donnelly used the profits to create and sell vinyl toys himself and numerous characters from his body of work—Accomplice, Chum, Bendy and BFF—followed suit.

As opposed to traditional fine art, Donnelly’s work in Japan was very much commercial. KAWS was a brand more than anything else, focused on product rather than original works or numbered editions. As a result, Donnelly felt that his work didn’t truly belong in galleries, or, rather, that traditional galleries would reject it outright. For instance, following a KAWS exhibit on the top floor of a Tokyo-area shopping center in 2001, Donnelly said, “if you told somebody in New York you were doing a show at the top of a shopping center, they’d be like, ‘Oh, that’s really tacky, commercial’ But over there, that was the normal outlet.”

Around the time of his exhibit, Donnelly was officially introduced to NIGO and the two began to work together, most notably on the Kimpsons exhibit—The Simpsons as seen by KAWS. Kimpsons was monumental not only because a Japanese streetwear heavyweight played a pivotal role, but because it set the stage for KAWS defining aesthetic: communicating ideas by utilizing universally recognized symbols and characters. Even after Donnelly KAWS-ified the characters, given the worldwide popularity of The Simpsons, each riff was instantly understood. No matter the nature of the image, the reference was apparent, now a KAWS signature.

After the success of Kimpsons, Nigo and KAWS began working on a collaborative BAPE collection. While not Donnelly’s first foray in clothing—Jun Takahashi approached Donnelly to design some clothing for Undercover in the late ‘90s, as did cult streetwear brand HECTIC and DC Shoes even made a largely forgotten KAWS sneaker—the BAPE x KAWS collaboration was the artist’s crossover moment. Donnelly worked with the label for three seasons, producing legendary pieces like the much-hyped KAWS x BAPE Companion full-zip hoodie and the coveted KAWS x BAPE Bapestas. Whether it was Donnelly’s cult-following in Japan, or simply BAPE’s notoriety, the collaboration was a massive success, and put Donnelly on the map as both a collaborator and as a streetwear force to be reckoned with all his own.

The collaboration trickled out between 2004-2005, coinciding with BAPE’s U.S. expansion and surging popularity in hip-hop. KAWS became a buzz-worthy name not only amongst rappers, but American street culture at large. As rappers began buying BAPE, they inevitably ran into the KAWS collaboration. By the latter half of the decade, KAWS wasn’t familiar to just Japanese tastemakers, but to Pharrell, Jay-Z and Kanye West, as well as anyone who followed street culture on the internet’s earliest forums and blogs.

In 2006, Donnelly partnered with Medicom Toy and Nexus7 to create brand that could fulfill his artistic aspirations as well as build of his streetwear buzz: OriginalFake. With a flagship store in Aoyama, OriginalFake utilized Medicom Toy’s extensive manufacturing capabilities and Nexus7’s streetwear know-how to create not only figurines, but graphic T-shirts and eventually full ready-to-wear collections. Apart from the usual KAWS characters that appeared as various graphics, the Chomper detail— comically wide teeth biting down—became a brand signature, appearing on the inside of jean waistbands and T-shirt collars. OriginalFake proved that for Donnelly, the line between art & clothing simply did not exist. Collective companions were just as important as logo-heavy outerwear.

Launched at the height of KAWS’ cultural dominance, OriginalFake was one of the most influential brands in streetwear, boasting a cult following both in Japan and abroad. Donnelly parlayed his brand’s success into collaborations with Nike and vans, respectively. In 2007, Vault by Vans released a massive collection celebrating The Simpsons. Spread over a slew of drops, Vault enlisted artists to create unique sneakers inspired by the fictional family. Donnelly was a natural choice, given KAWS’ “Kimpsons” exhibit, and allowed the artist to finally work with the beloved animated series in an official capacity.

A year later, Nike approached Donnelly as part of the Nike 1World project. The artist created a black and green X-laden Air Force 1—ironic given his previous work with BAPE on a handful of Bapestas—and two pairs of Air Max 90s. Despite newfound recognition in the West, KAWS continued to foster relationships in Japan, working alongside Hiroki Nakamura on a handful of Visvim sneakers between 2007 and 2008, particularly the Skagway and the Logan—itself inspired by Old Skools and Slip-Ons, fitting given Donnelly had worked with Vans just a year prior.

Therein lies the magic of KAWS. Donnelly has consistently subverted symbols—be they characters or sneakers—ingrained in the wider cultural psyche and transformed them into something else entirely. Whether its a Simpsons homage that inevitably leads to an actual Simpsons collaboration or a unique take on a high-fashion Japanese remake of a Vans’ silhouette, the line between appropriation, consumption and reinterpretation ceases to exist.

In 2008, Donnelly was tapped by Kanye West to create the iconic album artwork for 808s & Heartbreaks in 2008 alongside then creative director Willo Perron. A noted fan, Pharrell Williams became a patron of sorts, purchasing a number of KAWS’ paintings and sculptures and commissioning the artist to create SpongeBob Squarepants-esque paintings reminiscent of “Kimpsons.” Although his work became increasingly commercial at the end of the ‘00s, ironically it was only then that Donnelly began to receive recognition for more than simply his products, but his art as well.

In 2008 alone there were two major exhibitions of KAWS’ work in the United States, at Gering & Lopez Gallery in New York and at Galerie Emmanuel Perrotin in Miami, respectively. In February 2009, the Honor Fraser Gallery opened an exhibition highlighting KAWS paintings and sculptures. While the established art world had misgivings prior to the Honor Fraser show about an artist who in large part made toys for a living, it praised his ability to “to take art outside the confines of the museum and engage with the wider culture.” Parallels were drawn to both Andy Warhol and Marcel Duchamp, titans who dabbled in commercial art themselves.

At the turn of the decade, Donnelly transformed from respected figure to cultural titan. Gallery shows were multiplying, Companion was transformed into a balloon for the Macy’s Thanksgiving Day Parade, OriginalFake was at its peak and Donnelly was designing special labels for Hennessy and covers for New York Magazine. Then, in 2013, Donnelly unexpectedly announced that OriginalFake would cease operations. While little explanation was given at the time, recently Donnelley explained that “[he] was always thinking about the season approaching in the back of [his] mind. It [wasn’t] fun.”

Immediately following the closure of OriginalFake, Donnelly’s focus diverged. Clothing and sneaker collaborations were few and far between, whereas exhibits, new paintings and towering sculptures were unveiled with increasing regularity in 2014 and 2015. The once product obsessed creative had finally crossed over into the art world proper. Seemingly, he was intent to stay.

It could be argued that after growing up convinced he would never be a part of the establishment, when Donnelly was finally accepted by the art world, he turned his back on the subculture that helped launch his career. That sentiment surely contributes to why many are weary of KAWS success. He is the art world’s unabashed commercial starlet, a “sell out.” That doesn’t sit well either art or street purists alike.

By 2016, KAWS’ fashion footprint was essentially non-existent. Then, in February, 2016, Uniqlo announced a KAWS collaboration as part of its upcoming Spring/Summer UT collection. Nigo had recently joined Uniqlo as creative director, a relationship that Donnelly admits was crucial in fostering the partnership. The debut collection was simple, using KAWS’ beloved characters to create graphic T-shirts. Over almost three years, the collaborative partnership has evolved to include KAWS’ unique takes on Peanuts and Sesame Street, including plush dolls reminiscent of Donnelly’s earliest Japan-exclusive toys.

Donnelly followed up his return to streetwear by rekindling his relationship with Nike in 2017, this time working with Jordan Brand. In early March, the long rumoured Jordan Brand x KAWS collaboration was finally confirmed, the grey suede Air Jordan IVs. Equipped with glow-in-the-dark outsoles and the artist’s patented Xs on the heel, the ultra-hyped sneaker dropped alongside apparel that harkened back to the OriginalFake days, with oversized, cartoonish graphics. The KAWS Jordan IV elicited a response similar to the artist’s prized 2005 collaboration with BAPE. NBA players flexed them on-court and the shoes became the most coveted, and valuable, release of 2017.

The Jordan release was followed up with further Uniqlo UT collections, as well as new versions of his BFF in collaboration with MoMA and, finally, a wider release of the previously limited black suede Air Jordan IV. While intimately familiar to streetwear veterans, the string of collaborations between 2016-2017 helped put KAWS on the map for a new generation of culture fanatics.

Today, Donnelly strikes a delicate balance between street culture and the more bourgeois art world. Each new collaboration is carefully considered. In early 2018, he worked with Union—one of the most historic boutiques in the industry—to commemorate the opening of its Tokyo branch. In June, he collaborated with Dior Men’s for Kim Jones’ inaugural collection, creating not only the centrepiece for the runway show, but also a capsule collection that released in November, which saw Donnelly KAWS-ify Dior’s iconic bumblebee logo. The Dior release coincided with the release of KAWS’ latest collaboration with Uniqlo, focused on Sesame Street. On the art front, Donnelly released a new body of work, “GONE,” which Vanity Fair compared to Michelangelo’s “Pietà.” A bold defense of his work, Vanity Fair argued that “Michelangelo was considered a sellout by skeptics who frowned upon his commissioned works for being commercial,” something which KAWS is still a victim of as well.

While Donnelly laughed off that comparison, it is not entirely ridiculous. Over the past two plus decades, KAWS has played a vital role in erasing the boundaries between high and low. How many others are capable of working with Dior, Uniqlo and Jordan—brands that truly represent the entire spectrum of price points, luxury and mass availability—simultaneously? Better yet, how many have actually done so, while concurrently creating an art exhibit that tours across galleries and museums that world over? In that regard, KAWS is a rare talent. His recent resurgence only underscores as such.