In this review, we provide a bird's eye view of recent developments in the field of pressure-sensitive adhesives (PSAs) derived from renewable monomeric building blocks. This emerging research field has been driven by increasing sustainability requirements in the adhesive industry and bridges the gap existing between highly optimized petroleum-based synthetic PSA systems, which display superior performance but lack biobased content, and historical PSAs derived from naturally occurring biopolymers (e.g., starch and natural rubber), which provide more environmentally friendly bonding solutions but have inherent technical limitations that prevent their more widespread implementation in today's technically demanding applications. We critically reviewed a representative (and exhaustive) survey of recent synthetic approaches to the development of biobased PSAs from the academic (articles) and industrial (patents) literature categorized in two families: chain-growth and step-growth polymerization routes. Finally, we draw a parallel between renewable synthetic PSAs and nature's selfadhesive glues, highlighting how the synergy between green chemistry and biomimetic concepts could inspire the emergence of a new generation of smart, synthetic, biobased PSAs with differentiated properties that approach the ones that are found in the natural world and with a wide spectrum of potential applications in the industrial and medical sectors.