Beyond their beautifully crafted and mesmerising images revered by international audience and critics, the works of Hong Kong filmmaker, Wong Kar-wai, present melancholic tales of missed opportunities, repetition, regrets, lamentations, and mis-recognition. Time plays a central role in these works. At their hearts, Wong's films mourn for the loss of a potential humanity in a hyper-capitalist city - super-modernity that produces a disconnected space governed by a timeless time. In this paper, I present an analysis of Wong's films focusing on his 2005 work, 2046, through the prism of Walter Benjamin's philosophical writings. In particular, Benjamin's works on the Trauerspeils (or German mourning plays) and the German Romantics are used to formulate three main points: 1. Trauerspiel is a product of capitalism where the Messianic end is forever postponed and time is incomplete; this is fundamental for an interpretation of Wong Kar-wai's works; 2. Benjamin's speculative or immanent critique (developed from his in-depth engagement with the works of the German Romantics) allows an effective analysis of Wong's films that exposes their latent content (or Wahrheitsgehalt); 3. accessing the truth content of Wong's films presents a key to the practice of making perceptible elusive experiences - which Ackabar Abbas describes as these experiences that, 'the more you try to make [them] hold still in a reflective gaze, the more it moves under you'. Through this analysis, I identify strategies that form part of the practice of making the hidden perceptible as means to pursue and reveal truths: a task that is very pertinent to our present cultural politics.