This chapter talks about recordings or performers who dramatize some significant cultural negotiations among languages, cultural codes, generational conflicts, and gender relations affecting Jews as much as other immigrants to the United States. Jewface recordings reduce Hebrew vocabulary to a nonsensical minimum, and all that remains of Yiddish is a stereotypically Jewish accent that transforms the language from the European perception of a defective German into an American perception of defective English. One of the most prolific Jewish dialect comedians of the era, Monroe Silver, opens the Jewface compilation with the 1920 recording Pittsburgh, PA. The comedian who most vociferously maintained the subversive stance of Jewish humor, and in turn exerted the greatest influence on subsequent performers and writers, was Lenny Bruce. Like Portnoy and Lenny Bruce, Silverman performs her comedy at a border between an uninflected American culture and multiple marginalities of religion, race, gender, and sexuality.