Superman II (1980)/Superman Returns (2006) – 26 years

Bryan Singer infamously left X-Men: The Last Stand to direct this Superman film. This opportunity was only presented to him after the collapse of the notorious Superman Lives project under Tim Burton, starring Nicolas Cage. Rather than taking what material had already been worked on for that film, Singer went an entirely different route. He chose to honor the original Superman films starring Christopher Reeve by crafting a film set between the events of Superman II and III, and so Superman Returns was born. As such, this sequel and its predecessor has a gap of 26 years. However, even if you don’t count that as the proper gap between Superman films, Superman Returns still comes in 18 years after the last Christopher Reeve movie, Superman IV: The Quest for Peace, which released in 1987.