AbstractDielectric elastomer transducers (actuators and generators) possess great commercial potential because they allow for novel transducer designs and applications due to—amongst others—their flexibility and low weight. On the other hand, the flexibility and inherent softness of dielectric elastomers also pose restrictions on their use, since the thin elastomers may undergo destructive deformations under large loads or in large electrical fields. In order to design better dielectric elastomers, it is crucial to understand the underlying phenomena of how thin and elastic dielectric elastomer films undergo electrical breakdown. This understanding will allow for the design of dielectric elastomers with high electrical breakdown strength and thus open up the use of films in transducers at higher electrical fields and forces. Here, the study couples intrinsic electrical breakdown strengths with well‐described polymer and network characteristics, namely Kuhn parameters and cross‐linking density. The universality of the developed model is illustrated by comparison over a wide range of silicone‐based elastomers, such as prestretched elastomers and synthesized cross‐linked bottlebrush polymers, representing both filled and unfilled elastomers. This study paves a robust way for the molecular design of elastomers into high‐intrinsic electrical breakdown strength dielectric elastomers.