Twelve selected pepper (Capsicum annuum L.) cultivars, bred for mechanical harvesting (grouped ripeness) and adaptation to different cultivation cycles (short to long), have been characterized by their carotenoid pigment content and composition with the aim of producing high-quality paprika. A detailed analysis of the carotenogenesis was performed throughout the ripening process, but with special emphasis on the ripe stage, with the aim of selecting the best cultivar for paprika production. The MA1 cultivar (with grouped ripeness and very short cultivation cycle) showed the highest carotenoid content (12697.58 mg/kg dwt), followed by DN5 and RN2 cultivars with 11086.88 and 10393.29 mg/kg dwt, respectively. Most of the cultivars (MA3, RN1, LR2, LR7, DN3, DR6, Datler, and Mulato) showed a total carotenoid content in the range of 7000-9700 mg/kg dwt. In general, chlorophyll-retaining character was related to high carotenoid content (cultivars DN3, DN5, MA3, Mulato, RN1, and RN2). The general trend of the cultivation cycle was that the shorter the cycle, the higher the total carotenoid content (as exemplified by the cultivar MA1). The lowest total carotenoid content was found for the RR1 cultivar (4856.77 mg/kg dwt), which showed the longest cultivation cycle. Carotenogenic capacity of the cultivars has been discussed relative to total carotenoid content and the R/Y and Caps/Zeax ratios, the main quality traits for breeding cultivars for production of high-quality paprika. The cultivar MA1, with the highest total carotenoid content, high R/Y (2.11) ratio, and highest Caps/Zeax (9.85) ratio, was found to be the most suitable cultivar for paprika production in terms of carotenoid pigment biosynthesis capacity. Moreover, this cultivar has a short cultivation cycle and grouped ripeness, which are both important characteristics for a proper application of mechanical harvesting. The potential improvement of other varieties is also discussed.