KAWS, born Brian Donnelly, embarked on his artistic journey in the vibrant and gritty landscape of New York City's graffiti scene. His early work was not just an exploration of form and color but a rebellious assertion of identity and presence in the urban sprawl. This period of his career laid the foundational elements that would later become hallmarks of his globally recognized style.

In the early 1990s, as KAWS moved to New York City, he began to leave his mark on the city's visual landscape. Unlike traditional graffiti artists who focused on lettering and elaborate tags, KAWS was drawn to the visual impact of subverting existing advertisements. He meticulously reworked bus shelters, phone booths, and billboard ads, inserting his own characters and motifs into the commercial imagery. This act of artistic intervention was both a critique and a playful reimagining of the advertising that saturates urban environments. It was during this time that he developed some of his most enduring motifs, such as the crossed-out eyes that would become synonymous with his characters.

KAWS' graffiti was distinguished by its precision and clarity, standing out in a genre known for its spontaneity and speed. His interventions were calculated and executed with the skill of a trained illustrator, reflecting his background in illustration from the School of Visual Arts in New York. This approach to street art—viewing the city as a canvas for thoughtful and provocative installations—was relatively novel and positioned KAWS as a bridge between the street and the gallery. His work captured the attention of both the public and the art world, earning him a place in the broader conversation about the boundaries and possibilities of contemporary art.

As KAWS' street art began to gain popularity, his distinctive characters started to emerge as icons in their own right. His ability to blend commercial imagery with his unique aesthetic drew a cult following. Fans and collectors alike began to seek out his altered ads, marking the beginning of his transition from a street artist to a global art phenomenon. This early period of his career is crucial for understanding KAWS' artistic evolution, demonstrating his knack for subversion, his commentary on consumer culture, and his seamless navigation between high and low art forms.

This graffiti work laid the groundwork for his later ventures into toys, fashion, and large-scale sculptures, all of which bear the distinct signature of his early interventions in public space. By transforming advertisements into art, KAWS not only challenged perceptions of public and private property but also redefined the potential of street art to engage with and alter the visual landscape of urban life​ (Street Art Bio)​.