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To examine the role of gender discrimination and sexual harassment in medical students' choice of specialty and residency program.Anonymous, self-administered questionnaires were distributed in 1997 to fourth-year students enrolled in 14 public and private U.S. medical schools. In addition to reporting the frequency of gender discrimination and sexual harassment encountered during preclinical coursework, core clerkships, elective clerkships, and residency selection, students assessed the impact of these exposures (none, a little, some, quite a bit, the deciding factor) on their specialty choices and rankings of residency programs.A total of 1,314 (69%) useable questionnaires were returned. Large percentages of men (83.2%) and women (92.8%) experienced, observed, or heard about at least one incident of gender discrimination and sexual harassment during medical school, although more women reported such behavior across all training contexts. Compared with men, significantly (p ≤ .01) more women who reported exposure indicated that gender discrimination and sexual harassment influenced their specialty choices (45.3% versus 16.4%) and residency rankings (25.3% versus 10.9%). Across all specialties, more women than men experienced gender discrimination and sexual harassment during residency selection, with one exception: a larger percentage of men choosing obstetrics and gynecology experienced such behavior. Among women, those choosing general surgery were most likely to experience gender discrimination and sexual harassment during residency selection. Interestingly, correlations between exposure to gender discrimination and sexual harassment and self-assessed impact on career decisions tended to be larger for men, suggesting that although fewer men are generally affected, they may weigh such experiences more heavily in their choice of specialty and residency program.This study suggests that exposure to gender discrimination and sexual harassment during undergraduate education may influence some medical students' choice of specialty and, to a lesser degree, ranking of residency programs.