Phyllis Diller, often celebrated as "The First Lady of Stand-Up," emerged in the comedic world after trailblazers like Jean Carroll and Moms Mabley, yet she ascended to become one of the first female superstars in the realm of monology. Throughout the 1960s, she achieved significant success with hit records, played at top comedy clubs, appeared in films, and even headlined her own TV series. Remarkably, she continued to captivate audiences and fill venues thirty years later, becoming a comedic icon. Her longevity in such a highly competitive industry was a subject of her reflection: "I never tried to be a phony, never tried to be a star. A lot of performers try to be someone else. I never did." Born in Lima, Ohio, Diller attended Bluffton College, where she showcased her talents as a writer for the school newspaper and as a singer and pianist. After marrying Sherwood Diller, she transitioned from her aspirations of a musical career to becoming a full-time housewife, raising five children. Feeling unfulfilled and seeking additional income, she began writing comic articles for the local San Leandro News Observer. Inspired to transform her written jokes into a stand-up routine, she debuted at San Francisco's famed Purple Onion nightclub at the age of 37. Initially portraying a campy chanteuse, she sang witty songs and delivered arch one-liners that poked fun at cultural trends. Despite a rocky start, Diller caught the attention of comedy legend Bob Hope in 1959, who recognized her potential despite witnessing her "bomb marvelously." He saw courage and potential in her performance, which bolstered her self-esteem. Gaining confidence, she began delivering more personal, conversational material, often centered around her life as a housewife. Her humor about her husband "Fang" and her self-deprecating jokes became audience favorites, long past her divorce from Sherwood Diller in the mid-60s. Her comedic style, reminiscent of her idol Bob Hope, delivered a rapid-fire succession of one-liners, often accompanied by her distinctive laugh—a sound she described as a development from desperation and nervousness while awaiting the audience's reaction. Diller co-starred in several films alongside Bob Hope but found her greatest success in stand-up comedy, where she became a consistently popular performer. Despite her frustrations with the lack of recognition in other media, she ventured into recording a serious album and performed on Broadway, stepping into a role in "Hello Dolly." Her musical talents occasionally led her to appear with symphony orchestras in more serious concerts. Renowned for her generosity, Diller frequently performed for charity and openly shared her comedic wisdom with aspiring comedians. She credited Claude Bristol’s book "The Magic of Believing" as a significant influence, advocating for maintaining a positive mental attitude. In the 1980s, she gained almost as much notoriety for her multiple plastic surgeries as for her comedy, openly discussing her procedures and offering advice to others considering similar changes. Though single since the 1960s, Diller often enjoyed the company of handsome escorts, staying vibrant and active until the end of her career. Despite the constant interruptions from fans, whom she described as "the bane of my existence," she was gracious and frequently donned disguises, including a nun's habit, to maintain her privacy. Her humor and vitality were reflected in her fearless attitude toward life and death, famously stating that she was "going to be truly dead" with no expectation of an afterlife. Phyllis Diller's dynamic presence in the comedy world made her an unforgettable figure, characterized by her energy, unique laugh, and relentless delivery of humor. Her legacy endures as a testament to her pioneering spirit and unapologetic self-expression in an era when female comedians were rare.