As a teenager, Donnelly created the "KAWS" name (based on the way the letters looked—the word, in fact, has no meaning), which he painted on the roof of an area building so that he could see it outside while attending class in high school.[8] He went on to attend the School of Visual Arts in New York City, receiving a Bachelor of Fine Arts in illustration in 1996.

Renowned for blurring the boundaries between high fine art, commercial design, and pop culture, he is one of the most prominent contemporary figures in the modern art scene.He gained recognition by painting his trademark X-marked eyes over advertisements in public places like phone booths and bus stops.

In the late 1990s, he created COMPANION, a vinyl figure with a skull-and-crossbones head and crossed-out eyes. This signature character helped him bridge the gap between street art, high fashion, and commercial product design. Over the years, KAWS has collaborated with major global brands such as Nike, Uniqlo, and Dior, while also reimagining famous cartoon icons.

Today, KAWS lives and works in Brooklyn, New York. His work ranges from collectible vinyl toys to massive sculptures exhibited in major museums and public spaces around the world, making him one of the most famous contemporary artists of his generation.