Many liberal Jewish Americans wrestle with their apparently competing value systems; without the personal experience of the Holocaust, many do not identify with the need for Israel as a refuge. This “new” Jewish American, according to Andrea Most, has adopted a liberal Protestant ethos and loosened communal bonds that tied them together with other Jews. Many young, liberal American Jews, with incomplete knowledge of the history or politics of Israel and an identity filtered through progressive American ideals, are becoming disenchanted with the Jewish state. This chapter examines contemporary plays performed on American stages and how they shape and reshape Jewish Americans’ relationships with Israel. The plays are explored through their substance and the dialogue that emerges through their performance. There is a particular focus on generational divides in attachment to Israel, such as between a father who witnessed the horrors of Dachau and a son who asserts that the Holocaust is marketed and exploited to garner support for Israel in If I Forget. It then examines how the “theater of the real” influences reality, in the case of My Name Is Rachel Corrie, and sparks significant media controversy. The controversy generated by Seven Jewish Children includes damning reviews and two complementary plays in dialogue, Seven Palestinian Children and The 8th Jewish Child. Three of the plays discussed in this chapter had canceled performances, which caused a backlash against censorship. Finally, this chapter examines how the guilt and shame of Israeli Jews are portrayed and how they deal with questions of obligation and moral perplexity.