Introduction: Given the increasing global burden of mental illness, the existing shortage of psychiatrists internationally is a concerning development with a deteriorating trajectory. In 2016, only 5% of US medical students considered a career in psychiatry, and the situation is similar in other areas (e.g., European countries). Attracting medical students to the field of psychiatry is evidently necessary. This paper investigates European medical students’ attitudes towards psychiatry, their intentions to pursue psychiatry as a career, and the role of different factors such as personal experience and education on their interest in psychiatry. Methods: A cross-sectional survey was analyzed from 799 medical students in two European countries. Data was collected in 2016. Participants completed a survey on their attitudes towards psychiatry, their medical education regarding psychiatry, and personal experiences. Cross tabulations with chi-square tests were performed for inferential analyses using a significance level of 0.05. Results: The number of years spent in medical school, the students’ personal experiences, and the perceived quality of education was significantly associated with specialty choice and ranking of psychiatry relative to other specialties. Students’ exposure to internships, psychiatric placements, and their view on psychiatric instructors also played a significant role in choosing psychiatry as a profession. Conclusions: The systematic evaluation of students’ attitudes towards psychiatry and motivational factors for pursuing psychiatry as a specialty, such as psychiatric education in medical school and personal experience, can inform necessary changes in the recruitment of students to the field. Efforts must address the worldwide shortage of psychiatrists to effectively reduce the burden of disease associated with mental health and substance use.