Despite the increasing awareness and concerns about plastic pollution, plastic packaging and single-use plastic (SUP) consumption continues to increase yearly. Even developed countries fail to adequately, let alone comprehensively, recycle the wide variety of plastic waste. Consequently, many countries have imposed levies or bans to curb the reliance on SUP, initially targeting single-use plastic bags and, in later stages—extending their legislation to other SUPs. However, only a few countries have succeeded in instilling persistent changes in plastic packaging consumption habits. Several key factors can drive behavioral changes, including stakeholder engagement in policy development, public education and awareness raising, accessible and affordable plastic alternatives, and a robust deposit-return system with adequate infrastructure. Taking as an example case studies from 12 countries, this paper aims to understand what underpins the success or underlies the failure of seemingly similar legislative approaches toward minimizing plastic bag consumption. To complete this analysis, peer-reviewed journals, governmental pages and reports were consulted to gather information about various plastic bag and later—other SUP bans and levies. This paper discusses in depth why and how satisfactory results fail to emerge if the above-mentioned measures are neglected. Importantly, from the case studies analyzed, this paper argues that the efficacy of plastic reduction legislation is contingent upon the degree of retail sector engagement rather than the specific policy instrument deployed.