Ann Benson is married to her childhood sweetheart, Jerry Segal, and they have two grown children, actor/director/writer Robby Benson and fashion designer Shelli Segal, and four grandchildren. Benson has been acting her entire adult life. In her hometown of Dallas, Texas, she hosted the children's television show "Small Fry Varieties," written by her husband and was also seen in numerous TV commercials. A regular performer in Breck Wall's Bottom's Up revue, she also starred in award-winning topical satirical musical revues written and directed by her husband and co-produced by her. These revues played during the '50s and '60s in leading hotels and clubs across the country from the Adolphus Hotel in Dallas, the Schroeder Hotel in Milwaukee and The Petroleum Club in Oklahoma City to the Cotillion Room of the NYC's Hotel Pierre. When her son, Robby, was young, they performed together for four months at the Imperial Theatre in Tokyo in Donald Albery's "Oliver" as members of the original English cast.
She starred in summer stock productions of "The Women" as Sylvia, as Nancy in "Oliver," played the title roles in "Mame" and "Hello Dolly," portrayed Lady Thiang in "The King and I" and Hedy in "How to Succeed" and was the female lead in "The Boy Friend." She was also the resident leading lady at the Red Barn Theatre in Saugatuck, Michigan, where Robby won his first lead role as "Oliver."