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Although deep neural networks have been immensely successful, there is no comprehensive theoretical understanding of how they work or are structured. As a result, deep networks are often seen as black boxes with unclear interpretations and reliability. Understanding the performance of deep neural networks is one of the greatest scientific challenges. This work aims to apply principles and techniques from information theory to deep learning models to increase our theoretical understanding and design better algorithms. We first describe our information-theoretic approach to deep learning. Then, we propose using the Information Bottleneck (IB) theory to explain deep learning systems. The novel paradigm for analyzing networks sheds light on their layered structure, generalization abilities, and learning dynamics. We later discuss one of the most challenging problems of applying the IB to deep neural networks - estimating mutual information. Recent theoretical developments, such as the neural tangent kernel (NTK) framework, are used to investigate generalization signals. In our study, we obtained tractable computations of many information-theoretic quantities and their bounds for infinite ensembles of infinitely wide neural networks. With these derivations, we can determine how compression, generalization, and sample size pertain to the network and how they are related. At the end, we present the dual Information Bottleneck (dualIB). This new information-theoretic framework resolves some of the IB's shortcomings by merely switching terms in the distortion function. The dualIB can account for known data features and use them to make better predictions over unseen examples. An analytical framework reveals the underlying structure and optimal representations, and a variational framework using deep neural network optimization validates the results.