Phyllis Elaine Schlosberg

Phyllis Elaine Schlosberg, a champion for women's rights and a larger-than-life figure, of Provincetown, MA and New York City,passed away on April 21, 2021. Phyllis was born and raised in Boston. She graduated Everett High School with honors, and won a National Oratorical and Acting Contest presented by American humorist and TV host, Sam Levinson. She graduated Boston State College with a Bachelor of Science Degree in Education. She then attended Boston University and received her MFA in Theater. She was an Elementary School teacher in Everett, MA and a Principal of a private Greek School in New York City.
She moved to Provincetown in the mid 1960s. There she began her career as the owner and proprietor of the Draw Me a Circle Portrait and Art Studio, in partnership with her brother Paul. For nearly 50 years, she was the owner of the iconic Post Office Cafe and Cabaret, where she discovered singers, actors, and impressionists, many of whom went on to national acclaim. From 1979-87, she owned the Pilgrim House Hotel, which included restaurants and cabarets. Some of the award winning entertainers who appeared included Eartha Kitt, Sharon Mcnight, and Divine.
Phyllis was very charitable, generous and dedicated to her friends and family. She was predeceased by her late partner Diane Fernandez (Diane Z), who were lovingly together for 27 years. They were the absolute love of each other's lives. She was the daughter of the late David and Freda Schlosberg of Everett. She is survived by her brother, Bruce Schlosberg and his wife Karen of Plano, TX, and her brother Paul Schlosberg of Everett/Malden, MA. She was a beloved aunt of nephew Evan and niece Sara of Charlotte, NC, her niece Marisa Randall and her husband Joseph of Lynnfield, MA and niece Michela Schlosberg of Revere, MA. She was the great aunt of Evelyn and Jonathan Randall. She leaves her dear friend and companion, Laurel Williams of New York City, and her friend Betty Minerva Newman and her wife Phoebe Otis of Provincetown, MA. She will also be missed by the hundreds of employees, business people, and the year round local towns people of Provincetown.
A special thanks goes out to the late Abe Saada and Reggie Cabral, who mentored her throughout her career. An unapologetic Liberal Democrat, she was an ardent supporter of Civil Rights, Equal and Human Rights and American Democracy. In her business and personal life, she broke the “glass ceiling,” long before the term became popular. To express condolences and/or make donations in Phyllis’ name to: Helping Our Women of Provincetown http://www.helpingourwomen.org/
34 Conwell St, Provincetown MA 02657 (508) 487 – 4357.
Private graveside services were held.