Purpose: The purpose of this manuscript is to explore an assignment given to students in an online gender and leadership graduate course as a tool to help them think critically about how music influences perceptions of gender roles in both society and leadership. Design/methodology/approach: The assignment directs students to review the current Billboard "Hot 100" chart, which lists the top 100 songs in the United States each week based on sales and streams. Students are prompted to identify a song with gendered themes and discuss how the song portrays women and/or men, what gender stereotypes the song supports or refutes, and whether the messaging is positive or negative in nature. Finally, the students discuss ways that the message in the song could influence the listener's opinion about gender stereotypes and what effect that could have on gendered leadership issues. Findings: Students use this assignment as an opportunity to apply the course material that relates to the importance of gender representation and the influence of media on gender issues in leadership. Originality/value: Recommendations are provided to inspire creative ideas for leadership educators who seek to prepare students to understand organizational challenges related to gender issues in leadership.