Fyre Festival (Ja Rule & Billy McFarland)

Fyre Festival stands as the most catastrophic failure in celebrity event history. Promised as a luxury music festival on a private Bahamian island, it delivered disaster-relief tents, soggy cheese sandwiches, and stranded guests. The event’s collapse triggered two rival documentaries and criminal fraud charges, sending co-founder Billy McFarland to prison for over six years. Even among the worst ventures on this list, Fyre Festival is uniquely devastating: it outperforms #2 Trump Steaks in both financial loss (investors lost $26 million) and cultural infamy, spawning countless memes and legal precedents for influencer liability.