Combining the characteristics of click chemistry with the ability of controlled radical polymerization (CRP) to tailor polymers with specific macromolecular features affords a variety of precise synthetic tools to prepare functional polymeric materials. Due to the plurality of functional groups present in diverse (co)polymers, postpolymerization modification methods should be not only efficient, but also highly specific. The copper-catalyzed coupling of azides and terminal alkynes has shown particular promise as a means to prepare functional polymeric materials. Homo- and block copolymers were prepared by ATRP and subsequently derivatized to contain azido end groups. Reaction of these azido-terminated polymers with an alkyne-containing acrylate or methacrylate resulted in near-quantitative chain end functionalization to yield macromonomers with various polymerizable moieties, molecular weights, and chain architectures. This versatile method of incorporating polymerizable end groups should be applicable to a variety of (co)polymers prepared by ATRP and can, in turn, enhance accessibility to new graft/brush copolymers. Additionally, the advantages afforded by reversible addition-fragmentation chain transfer (RAFT) polymerization were combined with click chemistry by incorporating azido moieties into chain transfer agents that were then employed to prepare acrylamido and styrenics (co)polymers.