As part of a recent leadership conference at my university, undergraduate student leaders invited a poet and hip-hop artist as the keynote speaker. To the surprise of many, the artist spoke almost entirely about how he didn’t know anything about leadership and didn’t want to know about it, how he hated leaders, and how he didn’t trust anyone to be a leader, especially those who proclaimed to BE leaders. Adding more shock to the keynote, he heavily peppered the speech with disturbing profanity. The response to his speech was dismay from the administration, astonishment from the faculty, and great enthusiasm from the majority of the students. Those students resonated with his antileadership message, even though they had voluntarily attended the day-long conference designed to develop their leadership skills. The event left me struck by the paradox of our students’ fascination with this “notleader” at the same time they were voluntarily attending a leadership conference designed to build their leadership skills.