Social presence is central to the enjoyment of watching content together, yet modern media consumption is increasingly solitary. We investigate whether multi-agent conversational AI systems can recreate the dynamics of shared viewing experiences across diverse content types. We present CompanionCast, a general framework for orchestrating multiple role-specialized AI agents that respond to video content using multimodal inputs, speech synthesis, and spatial audio. Distinctly, CompanionCast integrates an LLM-as-a-Judge module that iteratively scores and refines conversations across five dimensions (relevance, authenticity, engagement, diversity, personality consistency). We validate this framework through sports viewing, a domain with rich dynamics and strong social traditions, where a pilot study with soccer fans suggests that multi-agent interaction improves perceived social presence compared to solo viewing. We contribute: (1) a generalizable framework for orchestrating multi-agent conversations around multimodal video content, (2) a novel evaluator-agent pipeline for conversation quality control, and (3) exploratory evidence of increased social presence in AI-mediated co-viewing. We discuss challenges and future directions for applying this approach to diverse viewing contexts including entertainment, education, and collaborative watching experiences.