Applications such as adversarially robust training and Wasserstein Distributionally Robust Optimization (WDRO) can be naturally formulated as min-sum-max optimization problems. While this formulation can be rewritten as an equivalent min-max problem, the summation of max terms introduces computational challenges, including increased complexity and memory demands, which must be addressed. These challenges are particularly evident in WDRO, where existing tractable algorithms often rely on restrictive assumptions on the objective function, limiting their applicability to state-of-the-art machine learning problems such as the training of deep neural networks. This study introduces a novel stochastic smoothing framework based on the \mbox{log-sum-exp} function, efficiently approximating the max operator in min-sum-max problems. By leveraging the Clarke regularity of the max operator, we develop an iterative smoothing algorithm that addresses these computational difficulties and guarantees almost surely convergence to a Clarke/directional stationary point. We further prove that the proposed algorithm finds an $ε$-scaled Clarke stationary point of the original problem, with a worst-case iteration complexity of $\widetilde{O}(ε^{-3})$. Our numerical experiments demonstrate that our approach outperforms or is competitive with state-of-the-art methods in solving the newsvendor problem, deep learning regression, and adversarially robust deep learning. The results highlight that our method yields more accurate and robust solutions in these challenging problem settings.