The political history of post-colonial Uganda is about as fascinating as that of any post-colonial state. The styles of key political figures, including Milton Obote and Idi Amin Dada, who have had the privilege of leading the country, are central to this fascination. Yet, since becoming Uganda’s leader in 1986, President Yoweri Museveni appears to have outdone his predecessors so much so that an entire generation cares little of the country’s history before Museveni. In 2021, the Ugandan people are scheduled to go to the polls in a presidential election. Following the success of a bill in parliament to expunge an upper age limit to contest for the office of president, the seventy-five -year-old Museveni is set to seek an additional mandate. Unlike in his previous electoral contests, however, Museveni faces the challenge of a man less than half his age. Thirty-seven year-old Robert Kyagulanyi is among the most successful popular musicians in East Africa. Kyagulanyi has since exploited his success and fame to become an elected Member of Uganda’s Parliament. Barely two years after the artist materialised as a politician, the Ghetto President, as he is popularly known, has declared his intention to run for the office Museveni occupies, against Museveni. Since Museveni permitted electoral contests for the presidency of Uganda, he has remained defiantly invincible. How does Kyagulanyi propose to undo this, and why does he think he can, to the extent of daring? Drawing on a socio-biographical analysis of the celebrity MP, some strategic interviewing and student-participant observation, the article engages the dynamics inherent with some of these issues.