We introduce random discrete Morse theory as a computational scheme to measure the complexity of a triangulation. The idea is to try to quantify the frequency of discrete Morse matchings with few critical cells. Our measure will depend on the topology of the space, but also on how nicely the space is triangulated. The scheme we propose looks for optimal discrete Morse functions with an elementary random heuristic. Despite its naiveté, this approach turns out to be very successful even in the case of huge inputs. In our view, the existing libraries of examples in computational topology are "too easy" for testing algorithms based on discrete Morse theory. We propose a new library containing more complicated (and thus more meaningful) test examples.