The straightness of rail joints is one of the critical factors affecting passenger comfort in high-speed railways, and investigating its influence on the dynamic performance of the vehicle–track system and riding comfort is of great significance. In this study, long-term field measurements were conducted at a turnout joint of a newly constructed high-speed railway in China, combined with multibody dynamics simulations, to systematically analyze the long-term evolution of rail joint straightness under various conditions, including pre- and post-grinding, joint commissioning, official operation, and extreme weather. Based on normalized data processing, the root mean square (RMS) index of joint straightness was extracted for feature quantification. Together with vertical acceleration and the Sperling index obtained from vehicle–track coupled dynamics simulations, a quantitative relationship between straightness and comfort was established. The results indicate that the cubic polynomial fitting method can effectively characterize the nonlinear mapping between the RMS of joint straightness and the Sperling index, further revealing a critical threshold at approximately 0.4 mm RMS beyond which vehicle running stability deteriorates and ride comfort significantly worsens. This study provides a reliable theoretical basis and engineering reference for the evaluation of rail joint quality and the optimization of maintenance strategies.