Certainty, control, and simplicity rule sociopolitical discourse in America. Easy answers and hasty conclusions are preferable to curiosity. But rigidity is stifling and evokes resentment, pain, and stagnancy. If we are to grow individually and collectively, we must embrace the grey, between extremes. ENIGMA, and its depiction of prominent characters demonstrates the importance of embracing nuance. Information on each subject abounds, but we can never describe the depth of their souls. While each is impactful, the portrait of their life is always incomplete to the viewer. Still, it’s easier to label and categorize. But their influence thrives not on their simplicity, but their complexity. Adversity, success, strength, weakness, integrity, and error make them dynamic, iconic, and enigmatic. These paintings seek to remind viewers that perspective shapes experience. These portraits, then, beg the question: Does objective truth exist? Or is reality an enigma? If so, is that scary or exciting? The answer is both, and that’s okay.