This study explored the experiences of first-generation and non-first-generation medical students in Saudi Arabia regarding their education, career aspirations, attitudes toward medical school, and perceived stress. We aimed to provide insights into the struggles faced by first-generation medical students. This cross-sectional study was conducted with 485 participants, 77.9% of whom were first-generation students. Data were collected using a questionnaire adapted from the Association of American Medical Colleges (AAMC) and analyzed using chi-square and Mann–Whitney tests. First-generation students were less decisive about future specialties, showed greater interest in taking the United States Medical Licensing Examination and the Professional and Linguistic Assessments Board exams, and expressed less interest in teaching roles than their non-first-generation counterparts. No significant differences were found in attitude, career considerations, quality of life, or daily activities. This study aligns with global calls for robust support programs, mentorship initiatives, and systemic interventions to enhance diversity and inclusivity in medical education. The research highlighted the importance of recognizing the diverse career aspirations and challenges first-generation medical students face. Tailored support programs are essential for fostering inclusivity in medical education, addressing unique needs, and enhancing students’ overall well-being. Future research should continue to explore the factors influencing the experiences of first-generation and non-first-generation medical students to contribute to ongoing efforts to improve medical education.