Surface topology has been shown to play a crucial role in the adhesive ability of gecko-inspired, embossed films. Herein, we report the use of Pattern Replication In Non-wetting Templates (PRINT) to design micro- and nano-embossed films in order to explore the relationship between surface chemistry, feature size, feature geometry, and shear adhesion. Ketone-containing elastomers were synthesized from various amounts of poly(ethylene glycol) diacrylate, 2-hydroxyethyl methacrylate, and 2-(methacryloyloxy)ethyl acetoacetate. Due to the presence of the ketone, elastomer functionalization was demonstrated with various oxyamine-, hydrazine-, and hydrazide-terminated ligands. Films were also shown to be non-cytotoxic for future applications in biomedically related fields. This system may allow for the design of flexible adhesives that can be selectively tailored for a range of applications.