There was a TV Show years ago (the early 2000s as I recall) on Showtime called Leap Years. The premise was it showed the lives of a group of friends when they were fresh out of college, the present (ie. the year the show was airing) which was five years after the early era and then the near future which was five years after the present. There were some clichés like one character was a struggling actress in the early era, a mega star in the present and a has been in the future but there were a few twists (one woman was married to one character in the present and a different one in the future, another character had two completely different careers). I have no idea if it holds up but I remember liking it at the time .
What is funny though is the show has almost no online presence at all. No old web sites, no reviews, almost nothing. It feels like I am the only person in the world who remembers it existed. Is there a show like that for you that it seems you are the only person who remembers it existed?