The document discusses four pioneering Playboy Playmates from the 1950s and 1960s who helped shape the magazine: - Bettie Page, the first bondage model, was Playmate in January 1955 and helped popularize fetish photography. - Elizabeth Ann Roberts, just 16, was the first underage Playmate in January 1958, sparking legal issues. - China Lee, in August 1964, was the first Asian American Playmate and had roles in films like What's Up Tiger Lily?. - Jennifer Jackson broke barriers as the first African American Playmate in March 1965 and faced controversy for her selection.