I delivered this presentation as part of the Dunedin School of Art (NZ)'s "Art and Money" symposium in August of 2013 (http://www.artandmoney.co.nz/). I argue that artistic works that mobilize money (coins, bills, etc.) as a medium or theme implicitly (and occasionally explicitly) grapple with what Frederic Jameson calls the "totality" of capitalism: the interconnected nature of a capitalist economy which enmeshes economic, social, political and cultural processes. Money appears to be a means by which art can grasp or represent that totality, and I illustrate three strategies artists take towards the topic. But I argue that, inevitably, picturing capitalist totality is impossible and doomed to failure, yet there may be something productive and disruptive about that failure. For more information check out http://ReImaginingMoney.net and http://maxhaiven.com.