Chuck Wein attended Taylor Allderdice High School in Pittsburgh, Pennsylvania, graduating in 1957. Following his secondary education, he went on to study at Harvard University in the early 1960s, where he met a young and beautiful Radcliffe heiress named Edie Sedgwick, reportedly in their psychiatrist's office. When Chuck decided to relocate to New York City, Edie, with her striking features, including fair skin, natural blonde hair, and blue eyes, accompanied him to the city, with Chuck convinced that the couple could become a power couple, impressing high society with their charm and elegance.
Recognizing Edie's great social potential, but also her tendency to be disorganized and lacking in self-promotion, Chuck took it upon himself to manage her life, acting as her promoter and introducing her to influential figures in the art world, including Andy Warhol in January 1965. Chuck became a regular visitor to Warhol's Factory, and, according to friends, meticulously planned their every move, carefully selecting the people Edie would meet and the activities they would engage in.
Chuck referred to himself and Edie as "mock elitists in fellowship," emphasizing his multifaceted role as her roommate, psychiatrist, astrologer, and Tarot instructor. His background in the Timothy Leary acid-experiment days likely influenced his unconventional approach to life and his fascination with the occult. During his time at the Factory, Chuck played a significant role in the creation of several films, including "Poor Little Rich Girl" and "Beauty #2," as well as conceiving "My Hustler" and "Ciao Manhattan."
However, Chuck eventually became disillusioned with life at the Factory and spent the remainder of the 1960s exploring the Far East, managing bizarre nightclub acts, and focusing on his interest in the occult.