The development of Jelekong painting can be understood through the ways in which artists negotiate inherited traditions, market demands, and personal artistic expression. This study examines the paintings of Iman Budiman to investigate how these three orientations are manifested through changes in colour, technique, materiality, and visual expression. Jelekong painting is conventionally characterised by established representational practices, including rural landscapes, bright colours, smooth brushwork, and sponge techniques. Using a qualitative approach based on observation, interviews, and documentation, this study identifies three coexisting modes of artistic practice in Budiman's work: traditional Jelekong painting, market-responsive textured painting, and personal-spiritual painting. The findings show that these modes do not constitute a linear chronological progression, but rather represent distinct orientations within the artist's practice. Traditional works retain established visual and technical characteristics as a cultural foundation; market-responsive works modify material and technical practices—such as using calcium carbonate and wood glue to produce thick textures—in response to consumer demand and production efficiency; and personal-spiritual works, particularly the series Suwung, provide a distinct space for personal and spiritual expression grounded in Javanese and Sundanese spiritual concepts. A Peircean semiotic analysis further examines the relationships among icons, indices, and symbols while distinguishing artist-stated meanings from researcher interpretations. Ultimately, this study demonstrates that contemporary Jelekong painting develops through selective retention, modification, and departure. This process highlights how Jelekong painting accommodates socio-economic adaptation and individual artistic exploration without abandoning its cultural grounding.