Controlled radical polymerization (CRP) is widely used to prepare a broad range of polymeric materials for diverse applications. One of the most important properties of CRP polymers is to maintain high livingness throughout the polymerization. Although such high end-group functionality has been overwhelmingly exploited for block copolymer synthesis in thousands of publications, it has rarely been explored for the polar opposite: reversing controlled radical polymerization and regenerating the monomer. In this talk, I will first discuss how, under thermodynamically favoured conditions, it is possible to depolymerize linear, bulky, cross-linked, and functional polymethacrylates made by RAFT polymerization. Notably, the depolymerization products can be utilized to either reconstruct the linear polymer or create an entirely new insoluble gel that can also be subjected to depolymerization. A solvent-free chemical recycling methodology that efficiently operates for both ATRP and RAFT-synthesized materials will also be presented. However, both depolymerization reactions are uncontrolled in nature (i.e. rapid monomerization of activated chains), providing no handle over the molecular weight and limiting further applications. To address this, our group developed a controlled depolymerization strategy that enables a linear decrease in molecular weight over time. Such gradual unzipping of polymer chains is not only useful for recycling purposes but also enables the structural characterization of various copolymers by facilitating the sequential release of monomers from the chain-end. At the end, I will discuss how we can potentially utilize the obtained knowledge to switch from “designer polymers” to commercially available materials containing undisclosed impurities.