It has been 25 years since Autumn and colleagues published their seminal research examining the adhesive forces generated by isolated gecko adhesive setae and identifying van der Waals forces as the major mechanism of adhesion in geckos. These findings served as the intellectual stimulus for thousands of studies aimed at synthetically replicating the form, function, and properties of gecko attachment, thereby establishing geckos as one of the most popular sources for biomimetic models to date. Despite these attempts to develop gecko-based synthetic adhesives (GSAs), several authors have noted that GSAs still fail to capture the performance and multifunctional properties exhibited by the natural system. In this chapter, we posit that the field of gecko-inspired adhesion represents an “inverted pyramid of observation and application,” whereby the explosive interest in replicating this organismal attachment system is founded upon a rather small number of empirical studies of limited taxonomic representation, species examined, and direct observations of setal attachment mechanics. We follow this with an overview of the immense diversity in the form and function of squamate fibrillar adhesive systems to provide researchers with the impetus to broaden the foundations upon which gecko-inspired adhesion is built. We then systematically review the 100 most-cited attempts to fabricate GSAs and assess their success in achieving the performance and properties of their natural counterpart. Subsequently, we employ this assessment to identify major successes and shortcomings of approaches to gecko-inspired adhesion and suggest avenues for future “biodiversity-aware” research that we propose will improve biomimetic designs and their functional outcomes.