The deviation of continuous and discrete complex random variables from the traditional proper and symmetric assumption to a generalized improper and asymmetric characterization (accounting correlation between a random entity and its complex conjugate), respectively, introduces new design freedom and various potential merits. As such, the theory of impropriety has vast applications in medicine, geology, acoustics, optics, image and pattern recognition, computer vision, and other numerous research fields with our main focus on the communication systems. The journey begins from the design of improper Gaussian signaling in the interference-limited communications and leads to a more elaborate and practically feasible asymmetric discrete modulation design. Such asymmetric shaping bridges the gap between theoretically and practically achievable limits with sophisticated transceiver and detection schemes in both coded/uncoded wireless/optical communication systems. Interestingly, introducing asymmetry and adjusting the transmission parameters according to some design criterion render optimal performance without affecting the bandwidth or power requirements of the systems. This dual-flavored article initially presents the tutorial base content covering the interplay of reality/complexity, propriety/impropriety and circularity/noncircularity and then surveys majority of the contributions in this enormous journey.