The pyridine moiety is a crucial structural component in various pharmaceuticals. While the direct ortho- and para-functionalization of pyridines is relatively straightforward, the meta-selective C-H functionalization remains a significant challenge. This review highlights dearomatization strategies as a key area of interest in expanding the application of meta-C-H functionalization of pyridines. Dearomatization enables the meta-functionalization through various catalytic methods that directly generate dearomatization products, and some products can be rearomatized back to pyridine derivatives. Furthermore, this article also covers the dearomatization of multiple positions of pyridine in the synthesis of polycyclic compounds. It offers a comprehensive overview of the latest advancements in dearomatization at different positions of pyridine, aiming to provide a valuable resource for researchers in this field. It also highlights the advantages and limitations of existing technologies, aiming to inform a broader audience about this important field and foster its future development.