The purpose of this study was to evaluate the in vitro effect of orthodontic bracket base shape on shear bond strength (SBS) to human enamel and assess the nature of debonding fractures using the Adhesive Remnant Index (ARI). Orthodontic brackets with different-shaped bases (flower, heart, rectangle) were bonded to 120 extracted human third molars. Shear bond strength was measured using a Servohydraulic Test System at 24 h and 2 months after bonding. Adhesive Remnant Index scores were evaluated under 10x magnification to assess the amount of resin left on the tooth. The control bracket (rectangular base shape) had the highest mean SBS (26.8 ± 8.2 megapascals [MPa]), and significantly differed from the flower (17.2 ± 4.4 MPa) and heart (18.9 ± 3.5 MPa) base shapes (p < 0.001). The mean SBS between debonding times at 24 h (21.5 ± 7.4 MPa) and 2 months (20.4 ± 6.7 MPa) were not statistically significant (p > 0.05). Analysis of ARI scores showed a significant difference between flower-24 h versus heart-2 months (p = 0.039), flower-24 h versus heart-24 h (p = 0.004), and control-2 months versus heart-24 h (p = 0.015). Bracket base shape influenced SBS, with the rectangular base shape having a higher mean SBS compared to flower and heart base shapes. Variations in ARI scores occurred based on bracket shape and were of a mixed adhesive-cohesive nature. All bracket shapes had bond strengths above the clinically acceptable range of 6-8 MPa, and may thus provide adequate SBS in a clinical situation.