Hollywood, as F. Scott Fitzgerald's self-pitying comment unwittingly suggests, was a place where Jewish and gentile fantasies mixed, met, and collaborated - in part because the former had to attract and the latter as part of their business. This chapter discusses four moments in the history of Jews and Hollywood: D. W Griffith's Musketeers of Pig Alley; Warner Brothers' Jazz Singer; Barbra Streisand's Yentl; Coen Brothers' A Serious Man. These films show the kinds of contortions and compromises by which Jews entered film first as objects then as (ambivalent) subjects; they demonstrate as well how Jews use the film industries to carve out new (and not unproblematic) itineraries for themselves in eras of ethnic revival, gender revolution, and postmodern hybrid identity formations challenging the very category Jew itself. A Serious Man tells us about Jews in the unfolding narrative of post-Hollywood film, and tells us about the concerns of baby-boomer generation Jews like the Coens.