Dielectric elastomer (DE) technology is based on the interactions of electrostatic charge with deformable polymer materials. While such materials and their electrical interactions have a long history of investigation, the discovery in the early 1990s that certain thin elastomer films, such as silicone films, were capable of supporting significant electric stress and producing large mechanical output increased interest in this phenomenon. This paper discusses the history of DE technology, presents developments, and considers future progress. Discoveries of large strain outputs with commercially available polymer films has allowed many researchers world-wide to research the technology and explore a wide range of applications. As the technology has matured, new modalities of the fundamental DE operation have emerged. In addition to actuators, researchers began to develop sensors and generators based on the technology. Additionally, explorations of the component materials, actuator geometries, electrode materials, packaging for environmental factors and high-voltage electronics are addressing the lifetime and other limitations of the technology. Examples addressing lifetime include: bistable and shape-memory configurations and self-clearing, carbon nanotubes electrodes. Improved modeling and failure mode investigations are also enabling the technology to progress. A number of commercial products based on DE technology have already hit the market. Although the impact of DEs thus far is well below that of other transducer technologies such as electromagnetics, their technical story and potential continue to expand.