Understanding the behavior of weak rock masses is important for predicting the stability of structures under different loading conditions. Traditional models such as the generalized Hoek–Brown and Coulomb weak plane are widely used; however, they often fail to capture the nonlinear and irreversible behavior of weak rock masses. This study offers a comprehensive overview of a critical analysis of constitutive models’ strengths and limitations for simulating weak rock masses. By comparing traditional and advanced novel approaches such as the strength degradation of rock (SDR) masses and continuous damage mechanics (CDM), this investigation shows that the new advanced methods significantly enhance the quality and accuracy of simulations. Moreover, SDR models address the limitations of classical plasticity models by incorporating nonlinear stress paths and irreversible stress changes, while CDM offers detailed insights into microstructural defect progression. These advancements allow for more accurate and practical predictions of long-term stability in geomechanical engineering tailored to specific requirements of each project.