Jewish humor, a modern Ashkenazi survival mechanism in the face of antisemitism, has recently been mobilized on digital streaming platforms by American women writers and performers, becoming a crucial mechanism of resistance to antisemitism and systemic misogyny. I analyze the narrative techniques and characters in Jewish humor employed by content creators to explore ethico-political questions raised by twenty-first-century media representations of Jewish American women. This dissertation maps the historical, technological, and economic factors that engendered these tropes. Following the influx of digital streaming platforms from 2005 to 2008, comedic content creators such as Ilana Glazer and Abbi Jacobson (creators of Broad City) and Rachel Bloom (creator of Crazy Ex-Girlfriend) began to mount productions with explicit representations of Jewish rituals, cultures, and subjects for niche audiences. These content creators adapted traditional motifs of Jewish humor by infusing their work with contemporary, popular feminist sensibilities and applying narrative tactics specific to digital technology. They infused their work with intertextual allusions (or brief, tongue-in-cheek insider references) to Jewish holidays, history, and feminist issues without explanation or contextualization. They inspired more established writers and performers (including Jenji Kohan (creator of Orange Is the New Black), Joey Soloway (creator of Transparent), and Natasha Lyonne (co-creator of Russian Doll)) addressing broader audiences, to incorporate similar references as Easter eggs or deep cuts to promote transmedia viewer engagement. These content creators developed and refined techniques such as parodies of older media representations of Jewish life (which include older antisemitic and misogynistic stereotypes, especially the Jewish American Princess and Jewish mother figures) to expose their limitations. Digital content creators engage in feminist midrash, a mode of storytelling, inspired by a form of biblical exegesis, that aims to answer and explore difficult ethical questions.In addition to fulfilling the requirements of a traditional, full-length dissertation, my project experiments with an innovative creative/critical writing methodology. My novel about a Jewish family in Los Angeles, incorporates all of the narrative techniques adopted by twenty-first-century comedic content creators to explore ethico-political questions raised by media representations of Jewish American women.