Sustainable employability (SE) refers to a worker’s extensive set of capabilities to make a valuable and healthy contribution over time. Due to the high fragmentation and precariousness of their working conditions, entertainment professionals’ SE is at risk. Methods: By considering valuable work, health, productivity, and long-term perspective capabilities as expressing entertainment professionals’ SE, this study explored the unique pattern of associations among entertainment professionals’ SE, conversion factors at personal (i.e., intrinsic motivation) and contextual levels (i.e., work–health balance external support and health climate, SE policies and social policies), and SE outcomes (i.e., life and job satisfaction and task performance), descriptive and network analyses were conducted in a sample of 123 Italian entertainment professionals. Results: Italian entertainment professionals’ SE was associated with factors at all levels of conversion. Conversion factors at the organizational level (i.e., SE policies and social policies) had a higher predictability (i.e., practical potential) in the SE network, compared to factors at the personal level (i.e., intrinsic motivation). Conclusion. This study added empirical evidence to SE models based on the capability approach, by showing the central role of contextual factors in the development of an extensive set of entertainment professionals’ capabilities.