Despite significant advances in numerical modeling of brake squeal, the majority of industrial research and design is still conducted experimentally. In this work we report on novel strategies for handling data-intensive vibration testings and gaining better insights into brake system vibrations. To this end, we propose machine learning-based methods to detect and characterize vibrations, understand sensitivities and predict brake squeal. Our aim is to illustrate how interdisciplinary approaches can leverage the potential of data science techniques for classical mechanical engineering challenges. In the first part, a deep learning brake squeal detector is developed to identify several classes of typical sounds in vibration recordings. The detection method is rooted in recent computer vision techniques for object detection. It allows to overcome limitations of classical approaches that rely on spectral properties of the recorded vibrations. Results indicate superior detection and characterization quality when compared to state-of-the-art brake squeal detectors. In the second part, deep recurrent neural networks are employed to learn the parametric patterns that determine the dynamic stability of the brake system during operation. Given a set of multivariate loading conditions, the models learn to predict the vibrational behavior of the structure. The validated models represent virtual twins for the squeal behavior of a specific brake system. It is found that those models can predict the occurrence and onset of brake squeal with high accuracy. Hence, the deep learning models can identify the complicated patterns and temporal dependencies in the loading conditions that drive the dynamical structure into regimes of instability. Large data sets from commercial brake system testing are used to train and validate the deep learning models.