Background: There is a paucity of data about the influence of surgical residents on the career choices of medical students. We hypothesized that medical students exposed to effective surgical residents would be more likely to pursue careers in surgery. Study design: From 1998 to 2003, 108 surgical residents were evaluated by medical students rotating on the third-year clerkship. Residents were scored on a 4-point scale (1 = outstanding to 4 = poor). The career choices of all medical students were also tabulated. Results: We examined 2,632 evaluations on 108 residents. Medical students who eventually pursued surgical residency training were exposed to surgical residents who were more effective clinical teachers, role models, and overall residents. In addition, medical students exposed to the highest-rated residents were more likely to pursue surgical residency training compared with students exposed to the least effective residents (12% versus 4.9%, p = 0.022). Conclusions: These data suggest that surgical residents who are effective educators and mentors influence medical students to pursue surgical careers. Efforts to provide more leadership and teaching workshops to surgical residents may not only create better future surgeon educators, but may also increase the number of students pursuing surgical training. © 2007 American College of Surgeons.