Hamlet 2 (2008, dir. Andrew Fleming) engages with Shakespeare playfully in both title and content, but to what end? The film has satirical fun playing with Shakespeare’s incongruous role in a farcical comedy, which ends with a re-write of Hamlet into a redemptive comedy. But the film also endorses a neoliberal notion of success that limits what this playfulness can achieve. The title plays with the possibility of a sequel to Shakespeare’s best-known tragedy; the content presents us with a protagonist, Dana Marschz (Steve Coogan), whose attachment to drama is the very embodiment of what Lauren Berlant calls “cruel optimism.” In Hamlet 2, playing with Shakespeare highlights the problematic nature of Dana’s emotional attachments, notably his love of acting and drama, in a neoliberal political environment. These attachments fit Berlant’s description of cruel optimism, in that Dana’s sense of self and the possibility of a prosperous future depend on his attachment to drama and to education, both of which are precisely the things that are ensuring he will not flourish. Furthermore, I also argue that the film’s improbable narrative of eventual success offers no way out of this environment. The absurdity of the film’s happy ending accepts a neoliberal conception of success as privatised, individualised, and decoupled from an adequately-funded education system. The impasse is broken for Dana, as if by magic, but the system that has denied him flourishing continues.