Statement of problem Whether deviations in the angulation discrepancy between the intercanine and interpupillary line significantly affect attractiveness is unknown. Purpose The purpose of this prospective study was to quantify dental and facial esthetics to determine whether smile angulation discrepancies in individuals identified as having attractive smiles are smaller than those in the average population. Material and methods An Internet search for “best smile” and “celebrity” identified 108 celebrities (Test group). Photographs showing smiles within 10 degrees of a frontal view were gathered. In mannequin testing, small head rotation (<10 degrees) was found not to affect the measurements. Photographs of dental students were used for the control group. The angulation discrepancy between the intercanine and interpupillary line was measured using computer software. Groups were compared using the Mann-Whitney U test (α=.05). Results Usable photographs were obtained for 94 celebrities (62 women, 32 men) and were compared with photographs of 97 dental students (54 women, 43 men). Significant (P<.01) differences in angulation discrepancy were found, with celebrities having smaller mean angulation discrepancies (0.97 degrees) than dental students (1.33 degrees). The differences between men and women were not statistically significant (P>.05). Conclusions Celebrities identified as having “best smile” had significantly smaller mean angulation discrepancies than the control group.