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This Reprint presents recent advances in the study of biomembrane models and their applications in understanding interactions between biological membranes and bioactive molecules. The collected articles combine experimental and computational approaches to investigate how membrane composition, lipid organization, cholesterol content, and membrane dynamics influence the behavior and activity of small molecules, peptides, proteins, and lipoproteins. The contributions included in this Reprint demonstrate the growing role of modern analytical techniques, including calorimetry, fluorescence microscopy, molecular dynamics simulations, and spectroscopy, in characterizing membrane structure and function. Particular attention is devoted to the relationship between membrane organization, lipid diversity, membrane heterogeneity, and biological activity. Several articles also explore the therapeutic relevance of membrane-associated processes in areas such as cancer research, inflammation, and drug delivery. Together, the studies emphasize the need for biologically relevant membrane models capable of reproducing the complexity of native cellular membranes. By integrating theoretical and experimental perspectives, this Reprint provides a comprehensive overview of current challenges and emerging directions in biomembrane science, offering valuable insight for researchers working in biophysics, pharmacology, medicinal chemistry, and related biomedical fields.