Background/Objectives: Cephalometric analysis has a pivotal role in the quantification of the craniofacial skeletal complex, facilitating the diagnosis and management of dental malocclusions and underlying skeletal discrepancies. This study aimed to develop a deep learning system that predicts a cephalometric skeletal parameter directly from lateral profile photographs, potentially serving as a preliminary resource to motivate patients towards orthodontic treatment. Methods: ANB angle values and corresponding lateral profile photographs were obtained from the medical records of 1600 subjects (1039 female and 561 male, age range 3 years 8 months to 69 years 1 month). The lateral profile photographs were randomly divided into a training dataset (1250 images) and a test dataset (350 images). Seven regression convolutional neural network (CNN) models were trained on the lateral profile photographs and measured ANB angles. The performance of the models was assessed using the coefficient of determination (R2) and mean absolute error (MAE). Results: The R2 values of the seven CNN models ranged from 0.69 to 0.73, and the MAE values ranged from 1.46 to 1.53. Among the seven models, InceptionResNetV2 showed the highest success rate for predictions of ANB angle within 1° of range and the highest performance in skeletal class prediction, with macro-averaged accuracy, precision, recall, and F1 scores of 73.1%, 78.5%, 71.1%, and 73.0%, respectively. Conclusions: The proposed deep CNN models demonstrated the ability to predict a cephalometric skeletal parameter directly from lateral profile photographs, with 71% of predictions being within 2° of accuracy. This level of accuracy suggests potential clinical utility, particularly as a non-invasive preliminary screening tool. The system’s ability to provide reasonably accurate predictions without radiation exposure could be especially beneficial for initial patient assessments and may enhance efficiency in orthodontic workflows.