Brake squeal—an audible high-frequency noise phenomenon in the range between 1 kHz and 15 kHz resulting from self-excited vibrations—is one of the main cost drivers while developing brake systems. Increasing damping is often a crucial factor in the context of self-excited vibrations. Countermeasures applied for preventing brake squeal have been investigated particularly for disk brakes in the past. However, in recent years, drum brakes have once again become more important, partly because of the issue of particle emissions. Concerning noise problems, drum brakes have a decisive advantage compared to disk brake systems in that the outer drum surface is freely accessible for applying damping devices. This paper focuses on the fundamental proving and evaluation of passive damping measures on a simplex drum brake system. To obtain a detailed understanding of the influence of additional damping on the squealing behavior of drum brakes, extensive experimental investigations are performed on a brake with an intentionally introduced high squealing tendency in the initial configuration. This made it possible to investigate the influence of different types of damping measures on their effectiveness. Techniques from the field of big data analysis and machine learning are tested to detect squeal in measured time series data. These techniques were remarkably reliable and made it possible to detect squeal efficiently even in data that was not generated on a traditional costly NVH brake dynamometer. To investigate whether the simulation method usually used for the simulation of brake squeal is applicable to depicting the influence of additional damping in drum brakes, a complex eigenvalue analysis was performed with Abaqus, and the results were compared with those from the experiments.