Wayne Thiebaud's cityscapes, like much of his work, blend the familiar with the extraordinary, transforming urban landscapes through his unique perspective and technique. His cityscapes diverge from his iconic depictions of everyday objects and sweets, instead presenting dramatic new perspectives on urban landscapes. Thiebaud's cityscapes are known for their bright, thick application of paint and severe depictions of steep inclines and long shadows, which add a dramatic flair to the ordinary scenes of city life. Born in Arizona and making his career primarily on the West Coast, Thiebaud's work, while often associated with Pop Art, diverges in its embrace rather than critique of American society and consumer culture​ (Art Market Magazine)​.

One of his notable pieces, "Sunset Streets" from 1985, showcases Thiebaud's unique approach to the cityscape genre. Held in the collection of the San Francisco Museum of Modern Art (SFMOMA), this oil on canvas painting is a vivid example of how buildings and streets can cling precariously to exaggerated, plunging hills, often intersected by steep freeways. Thiebaud crafted many of these works from memory, suggesting not a specific location but his overall sense of the city's essence. His cityscapes straddle the delicate balance between representation and abstraction, exploring formal problems of proportion, size vs. scale, and spatial relationships​ (SFMOMA)​.

Through his cityscapes, Thiebaud invites viewers to see urban environments anew, rendering the vertiginous views of cities like San Francisco in ways that are more real than one might assume without having visited. These works highlight his fascination with the varying viewpoints within urban landscapes, merging different elements into a cohesive whole. His work in this genre exemplifies a broader trend in his oeuvre: the transformation of the mundane into the sublime, demonstrating his mastery over the medium and subject matter​ (ART & ARTISTS)​.

Thiebaud's contribution to the art world extends beyond his paintings. His career also included significant periods of teaching, notably at the Sacramento Junior College and the University of California at Davis, where he influenced generations of artists with his insights into painting and art history. As a figure whose work spans the gap between Pop Art and a more nuanced exploration of American life, Thiebaud's cityscapes represent a key component of his legacy, inviting viewers to reconsider the landscapes of their everyday lives through his eyes.