Within a year of emancipating herself from foster care at age 17, Featherstone became Canada's top model when her September Flare magazine cover broke all previous records for sales.
She is best known for playing the Maid on Seinfeld, Chloe in Friends, and the fiancée (Linda), who left Adam Sandler's character (Robbie) at the altar in The Wedding Singer.
[2] Featherstone has created sitcoms for Sony, DreamWorks, and NBC television and has written nonfiction for Time, Jane, Flare, Huffington Post, Dame, and Zoomer.
As a director, she combines her years of experience in fashion as a model; working with important photographers and magazines such as; Italian, French, and American Vogue, Mademoiselle, Seventeen, Sassy, Harper's Bazaar Italia, Grazia, Harpers & Queens, Albert Watson, Bruce Weber, Irving Penn, her love of cinema and decades in the film industry; a refined sense of story as an oft published essayist; her passion for philosophy; and a love of creating safe spaces for collaboration, into a movement of aesthetic bliss.
Since 2009, she has studied moral and spiritual psychology with Rabbi Mordecai Finley, Ph.D.[citation needed] She served as a consultant on Cracked Up, a Netflix documentary about the effects and healing of trauma.