The olefin metathesis reaction has showed promising application in rubber chemistry and industry in the last decades for the production of specialty rubbers (polyene rubbers, low-molecular-weight telechelic oligomers, hydrogenated diene-based rubbers, liquid rubbers, and other functional rubbers) and characterization and recycling of rubber products (waste tires or others) via ring-opening metathesis polymerization (ROMP) or the cross-metathesis (CM) degradation technique. Here, recent advances in both molecular modeling and experimental investigations of the olefin metathesis reaction in rubber chemistry and industry are reviewed, and the challenges of future applications are also prospected.