Phyllis Elaine Schlosberg, of Provincetown and New York City, a larger-than-life figure who gave many young performers their start, died on April 21, 2021. She was 81.
Phyllis was born and raised in Boston, the daughter of David and Freda Schlosberg. She got her acting start at Everett High School, winning a national contest presented by American humorist and TV host Sam Levenson. She graduated from Boston State College with a B.S. in education, then earned an M.F.A. in theater at Boston University. She was an elementary school teacher in Everett and later the principal of a private school in New York City.
Phyllis moved to Provincetown in the mid 1960s. She began her career here as co-owner, with her brother Paul, of Draw Me a Circle Portrait and Art Studio. For nearly 50 years, she was the owner of the Post Office Café and Cabaret. From 1979 to 1987, she owned the Pilgrim House Inn.
She discovered and mentored many singers, actors, drag performers, and impressionists, some of whom went on to national acclaim. Among them: Eartha Kitt, Lea DeLaria, Divine, Carol O’Shaughnessy, Elvira, and Sharon McNight. McNight won a Golden Gull (an award created by Horace Stowman and Mark Cross of Ocean’s Inn) and gave it to Phyllis.

“I basically owe my career to Phyllis,” said Jeffrey Roberson, a.k.a. Varla Jean Merman, this week. Phyllis saw Roberson perform in New York City and persuaded him to quit his day job in advertising and come to Provincetown. “She didn’t play games,” he said. “But she knew talent that would sell in Provincetown.”
Phyllis also discovered singer Jimmy James, saving him from a nightmarish job performing at a casino in Atlantic City. “She championed me, she encouraged me, she taught me the ropes of how P’town works,” he said. “She was a mentor in so many ways.” A savvy businesswoman, Phyllis was also “the life of the party,” said James. “Losing her feels like the end of an era.”
Phyllis was fiercely and unapologetically liberal — an advocate for civil rights and women’s rights. She was also generous and dedicated to her friends and family. She was predeceased by her partner, Diane Fernandez, who owned the clothing store Diane Z. Together for 27 years, they were the loves of each other’s lives.
She is survived by her brothers, Bruce Schlosberg and wife Karen of Plano, Texas, and Paul Schlosberg of Everett and Malden. She was a beloved aunt to Evan and Sara Schlosberg of Charlotte, N.C.; Marisa Randall and husband Joseph of Lynnfield; and Michela Schlosberg of Revere. She was the great-aunt of Evelyn and Jonathan Randall. She also leaves her dear friend and companion Laurel Williams of New York City, as well as her friend Betty Minerva Newman and wife Phoebe Otis of Provincetown.
She was predeceased by brother Paul’s wife, Christine Luongo.
Memorial donations in Phyllis’s name may be made to Helping Our Women, 34 Conwell St., Provincetown 02657 (or helpingourwomen.org). Private graveside services were held in Melrose. For online condolences, visit goldmanfc.com.