Work is a significant part of everyday life for many, so it is not surprising that it would be included in the storylines of many Hollywood films. Movies incorporate elements from everyday life, real or imagined. There is a plethora of research making connections between film and the social world, but not regarding workplace bullying. This study takes a close and in-depth look at workplace bullying as it is depicted in scenes from a sampling of 100 Hollywood films released 1994-2016. It is interpretive in nature and guided by the theoretical underpinnings of film theory, social construction of reality theory, and symbolic interaction theory. Qualitative media analysis (synonymous with ethnographic content analysis) and grounded theory, in concert with Hymes Ethnography of Communication SPEAKING Model methods, blended and facilitated data collection and analysis. The advent of a theoretical frame highlighting the delicate interplay within the depictions of workplace bullying became evident; herein named the paradoxical web of workplace bullying. Within this paradox are tragedy and comedy; from which ambivalence resilience theory emerges. This research contributes to the literature of conflict studies and more specifically the scholarly research and professional practice dedicated toward greater understanding and eradication of this horrific phenomenon, workplace bullying