The early initiation of tobacco use by the youth is the basis to advocate for the tobacco-free generation (TFG). The basis is to prevent the sale and supply of tobacco to individuals born after a certain year or after a specified year. This cohort approach on educating the generations to be tobacco-free was first conceived by an Australian Mathematician Jon Berrick. This is based on the concept of rite of passage that connects smoking to adulthood and encourages youth approaching that age of smoking. Education and awareness would certainly empower the younger generation to never ever use tobacco. The TFG models have been replicated in Singapore within the set time-bound goals. An integrated and common risk approach with effective compliance and enforcement remains the single best approach in prevention, so is the concept of TFG which also works well with other tobacco control measures through its optimal integration. With this background, we aim to review the concept of TFG toward the endgame of tobacco among the youth to eliminate this existing epidemic. Furthermore, it hopes to provide a deeper understanding about the best practices in the implementation, enforcement, and various challenges associated with compliance of this proposal in various regions of the world toward the endgame.