KAWS' Package Painting marks a pivotal period in his career where his work deeply explored the intersection of fine art and commercial product through a unique presentation style. Originating around the year 2001, coinciding with his first solo exhibition in Tokyo, these works were inspired by beloved animated sitcom characters, encapsulated within the same type of plastic blister packaging commonly used by toy manufacturers. This series represented KAWS' initial foray into the realm of 'fine' art with a deliberate approach that cleverly navigated the space between painting and product, art and commerce.

A notable aspect of this series is its blend of accessibility and artistry, creating a bridge that spans across collectors of commercial merchandise and fine art enthusiasts alike. The series included some of KAWS' first formal paintings on canvas, presenting a fascinating mix of his anarchic painterly style with the polished finish of animation acrylic paints, typically used by animators for their vibrant and enduring quality. These early works were not only critical in establishing KAWS' artistic identity but also in showcasing his ability to disrupt traditional classifications of art, making a statement on the consumer culture's impact on art and vice versa.

One of the standout pieces in this series, titled "UNTITLED (KIMPSONS #1)," was created for NIGO®, the founder of A Bathing Ape®. This piece, among the largest of the KIMPSONS paintings commissioned by NIGO®, symbolizes the quintessential essence of KAWS’ disruptive and engaging artistic approach. The fact that these works were commissioned by one of the most visionary cultural entrepreneurs of the time added a layer of significance, situating KAWS’ work within a broader context of cultural commentary and critique.

KAWS’ ability to navigate between the worlds of commercial product design and fine art painting with the "Package Painting Series" exemplifies his unique position in the art world. His work challenges viewers to reconsider the value and categorization of art in contemporary society, blurring the lines between what is considered 'high' and 'low' art. This series is a testament to KAWS' ingenious approach to art-making, where he consistently questions and subverts the norms of artistic expression and consumer culture​ (Sothebys.com)​.