There have been a wide variety of efforts to develop conductive elastomers that satisfy both mechanical stretchability and electrical conductivity, as a response to growing demands on stretchable and wearable devices. This article reviews the important progress in conductive elastomers made in three application fields of stretchable technology: stretchable electronics, stretchable sensors, and stretchable energy harvesters. Diverse combinations of insulating elastomers and non-stretchable conductive materials have been studied to realize optimal conductive elastomers. It is noted that similar material combinations and similar structures have often been employed in different fields of application. In terms of stretchability, cyclic operation, and overall performance, fields such as stretchable conductors and stretchable strain/pressure sensors have achieved great advancement, whereas other fields like stretchable memories and stretchable thermoelectric energy harvesting are in their infancy. It is worth mentioning that there are still obstacles to overcome for the further progress of stretchable technology in the respective fields, which include the simplification of material combination and device structure, securement of reproducibility and reliability, and the establishment of easy fabrication techniques. Through this review article, both the progress and obstacles associated with the respective stretchable technologies will be understood more clearly.