Stellar fundamental properties (masses, radii, effective temperatures) can be extracted from observations of eclipsing binary systems with remarkable precision, often better than 2%. Such precise measurements afford us the opportunity to confront the validity of basic predictions of stellar evolution theory, such as the mass-radius relationship. A brief historical overview of confrontations between stellar models and data from eclipsing binaries is given, highlighting key results and physical insight that have led directly to our present understanding. The current paradigm that standard stellar evolution theory is insufficient to describe the most basic relation, that of a stars mass to its radius, along the main sequence is then described. Departures of theoretical expectations from empirical data, however, provide a rich opportunity to explore various physical solutions, improving our understanding of important stellar astrophysical processes.