The development of various controlled radical polymerization techniques as well as site- and residue specific strategies to modify peptides/proteins with synthetic polymers have made polymer chemistry a powerful tool to address materials problems at the biology interface. This article will present recent examples for bioactive surface modification and polymer therapeutics; it will highlight the use of controlled radical polymerization techniques and bioconjugation strategies to develop surface coatings for regenerative medicine and diagnostics, respectively, polymer-based nanomedicines.