Gilligan’s Island, the iconic TV series, harbors a trove of intriguing behind-the-scenes tales. From the ongoing debate about Gilligan’s first name to near misses in casting, such as Carol O’Connor as the Skipper and Raquel Welch as Mary Ann, the show had its share of twists. Real-life wealth, dark character twists in a 2003 satire, and unexpected tie-ins with other shows added layers to the narrative. The cast experienced on-set injuries, age deception, and even a rejected theme by John Williams. Despite bloopers making it to the final cut, the show became a cultural phenomenon, with enduring mysteries and anecdotes that continue to captivate fans.