This problem happens with people making their lists of favorite movies, as well; the newer movies are the ones more people have seen so they make more peoples' lists. But if you sort movies by box office take adjusted for inflation, you then get Star Wars and Gone With The Wind in the top 5, instead of Avatar and Titanic.
Unfortunately, we don't have any way to compare pinball machines like we have the box office take for movies, but the analogy is still workable. Movies like Citizen Kane were pioneering movies of their day; they established conventions that are still used in movies to this day, but if you tried showing it to a group of teenagers nowadays, they would likely find it too slow-paced and boring. Thus it is with pinball; you can't even really compare straight-up pinball machines like Space Shuttle and Twilight Zone. Even though Space Shuttle was a great machine for its day, it seems hopelessly quaint when compared to all there is to do in Twilight Zone. Yet Space Shuttle is still a great machine.