A growing body of research explores the experiences of students in graduate education and more-particularly, students of color pursuing advanced degrees. However, little research provides information about Black students' aspirations to pursue graduate education in science, technology, engineering, and mathematics (STEM). Even less is known about Black males' aspirations to pursue graduate education in STEM. Knowing why Black males aspire to pursue graduate education would assist stakeholders (e.g., administrators, faculty, advisors, family members, and peers) in better supporting and motivating students while they are in graduate school, or earlier in their educational trajectories. This retrospective study of 50 Black males' aspirations for graduate school aimed to better understand the factors that influenced their aspirations to pursue graduate degrees in engineering. Four themes were most influential: (a) Black male students received messages implying that a bachelor's degree was insufficient, (b) earning a graduate degree in engineering was regarded as a sign of community influence and respect, (c) students' professorial career goals necessitated an advanced degree, and (d) mothers functioned as support systems and role models for earning an advanced degree. Finally, we offer implications for future research and practice. These new findings about aspirations regarding graduate education will assist stakeholders in identifying critical moments and experiences necessary to encourage talented individuals to pursue advanced degrees in STEM fields.