Bill & Ted’s Bogus Journey (1991)/Bill & Ted Face the Music (2020) – 29 years

Starting with the latest sequel announced, we have the third adventure for the lovable duo of Bill & Ted. Though rumored to be in development the last few years, with Keanu Reeves’ resurgence in popularity, the sequel was officially announced by Reeves and Alex Winters earlier this year with a release date set for 2020. The film will see Bill & Ted now as middle-aged dads still trying to fulfill their destiny and crank out a hit song 29 years after the release of 1991’s Bill & Ted’s Bogus Journey.