Background: Cannabis is the most widely used illicit substance, particularly among youth. Earlier onset is associated with poorer clinical trajectories in cannabis use disorder (CUD), but its relationship with hedonic–motivational components remains unclear. Methods: Outpatients with severe CUD (n = 121) were stratified by age at onset (<18 vs. ≥18 years) and compared on hedonic–motivational functioning using the Snaith–Hamilton Pleasure Scale (SHAPS) and the Temporal Experience of Pleasure Scale (TEPS). Healthy subjects (n = 112) served as a reference group. Results: CUD groups were comparable in clinical characteristics and cannabis use patterns. TEPS-Anticipatory scores were lower in patients with onset before age 18 (p < 0.001) and remained associated with onset group after adjustment for gender, education, and CUD duration (p < 0.001). When healthy subjects were included, significant group effects were observed (p < 0.001). Post hoc comparisons confirmed reduced TEPS-Anticipatory scores in early-onset vs. both later-onset and control groups, and higher SHAPS scores in both CUD groups vs. controls. Conclusions: CUD onset before age 18 is associated with reduced anticipatory pleasure, suggesting a greater involvement of anticipatory than other dimensions of hedonic functioning. Age at onset may therefore help identify patients with greater motivational vulnerability and inform early, targeted prevention and intervention strategies.