Childhood obesity has profound effects on puberty in boys and girls, altering its timing, progression, and associated hormonal changes. Also, later male fertility could be impaired by childhood and pubertal obesity in light of the impact of inflammatory markers on semen quality. The aim of this narrative review is to explore the intricate relationship between childhood obesity and its impact on pubertal development and fertility, with a specific focus on boys. Such a relationship between obesity and pubertal timing in males is highly influenced by metabolic, hormonal, genetic, epigenetic, and environmental factors. While many studies suggest that obesity accelerates pubertal onset in boys, some studies do not confirm these findings, especially in cases of severe obesity. In fact, delayed puberty has also been reported in certain instances. Obesity influences fertility through different central and peripheral processes, including an altered endocrine milieu, inflammatory environment, and epigenetic modifications that alter semen quality and vitality, leading to subfertility or infertility. The early identification and management of potential issues associated with obesity are crucial for ensuring optimal reproductive health in adulthood. Further research is essential to clarify these associations and to develop targeted interventions aimed at preventing the negative health outcomes associated with obesity-related disruptions in puberty and fertility.