Research on dielectric elastomer generators (DEGs) which can be utilized to convert mechanical energy to electrical energy has gained wide attention lately. However, very few works account for the operating temperature, viscoelasticity and current leakage in the analysis of DEGs simultaneously. In this study, under several compound four-stroke conversion cycles, the electromechanical performance and energy conversion of a dissipative DEG made of a very-high-bond (VHB) elastomer are investigated at different operating temperatures. The performance parameters such as energy density and conversion efficiency are calculated under different temperatures. Moreover, the common failure modes of the generator are considered: material rupture, loss of tension, electrical breakdown and electromechanical instability. The numerical results have distinctly shown that the operating temperature plays an important role in the performance of DEGs, which could possibly make a larger conversion efficiency for the DEG.