Objective: Adolescence is a developmental stage of critical changes in sleep and its circadian timing when the contribution of abnormal sleep variability (amount) and sleep regularity (timing) to obesity and its associated adverse cardiometabolic health outcomes appears to increase. The aim of this study was to summarize findings from studies conducted in adolescents examining both sleep variability and regularity in relation to obesity and cardiometabolic health. Gaps in research and potential causal pathways that future studies should examine are highlighted. Results: Nightly deviations in sleep duration and sleep midpoint appear to contribute to the development of obesity and associated adverse cardiometabolic outcomes in youth. Studies show that increased sleep variability and irregularity are associated with obesity, decreased physical activity, dysregulated eating and inadequate diet, metabolic dysfunction, impaired cardiac autonomic balance, and elevated blood pressure in adolescents. Conclusions: A stable circadian timing of sleep is essential to the overall physical well-being of youth. Emerging evidence supports that sleep variability and circadian misalignment, including sleep irregularity, contribute to adverse obesity-related health outcomes early on in adolescence. Future studies should focus on the underlying behavioral and biological mechanisms in the causal pathway between day-to-day deviations in the amount and timing of sleep and obesity.