Rudolph Weisenborn was born in Chicago to German parents and tragically orphaned at age nine, leading to a nomadic youth before settling in Colorado, where he worked as a cowboy and gold miner. In Denver, he attended the Students’ School of Art for four years under the tutelage of Henry Reed and Jean Mannheim, both esteemed artists. Following a conventional academic path, Weisenborn spent two years drawing from casts before advancing to live models. Despite early adherence to traditional methods, he soon rebelled against what he perceived as stifling constraints in art, remarking, “It took me ten years to get it out of my system.”

Returning to Chicago, Weisenborn emerged as a key figure in the modernist movement, challenging traditional art norms to embrace Cubism and becoming a leader in avant-garde and radical art circles in the city. His influential career saw him involved in various art groups such as the Palette and Chisel Club, the American Artists' Congress, and founding the Chicago No-Jury Society of Artists and No Jury Exhibitions. He also taught at the Chicago Academy of Fine Arts from 1922 to 1964 and established the Weisenborn Art School in Oak Park, IL.

Notably, Weisenborn was a founding member of the American Abstract Artists (AAA) and later taught privately until 1964. While historical confirmation is lacking, contemporary critics suggested he might have been the first Chicagoan to exhibit an abstract painting at the Art Institute of Chicago. He certainly played a pioneering role in breaking away from representational norms prevalent in the Art Institute's annual exhibitions.