The 'black hole' is a signifier that pervades contemporary experience, conveying the 'gaps' and 'voids' in Western culture and psyche. Depth psychology stemmed from the growing uncanniness of city and psychic spaces during the 19(th) century. There was an emerging fascination with the 'dark Thing'--the 'It' of many names. Like a pandemic, depictions of the 'black hole' experience have continually emerged in the tragic events and cultural malaise of the twentieth and twenty-first centuries. Art, philosophy, science, psychoanalysis, literature, and cultural studies have variously articulated this frighteningly potent, yet endlessly elusive signifier. A many-sided, dialogical process best provides acquaintance with such a complex phenomenon. Multiple examples and perspectives, as well a detailed case study, will delineate some of its dimensions. They will show that such 'black hole' encounters are not merely negative, but are often the enigmatic source of new awareness and creation.