Understanding the key factors influencing the mechanical and electrical properties of semiconducting polymers is crucial to the development of stretchable electronics. In this work, a high-mobility diketopyrrolopyrrole-based conjugated polymer with varied number-average molecular weights (M-n) was used as the model system to explore the impact of molecular weight on the electrical and mechanical properties. Higher-M-n films are more ductile and stretchable. Both hole mobilities of thin-film transistors and elastic modulus become maximum at a moderate M-n of 88 kg/mol. It was found that film continuity, entanglements, and relative degree of crystallinity are critical factors for approaching the best device performance and highest elastic modulus. The transition molecular weight of a given polymer semiconductor is the key to achieving stretchable high-mobility transistors that are practically useful. This work would help to offer guidance to manipulate the mechanical and electrical properties for other polymer semiconductors.