3. Sports Night (1998-2000)
The TV Show: One of the several shows on this list that was just too far ahead of its time, Sports Night was a critically acclaimed series that followed the inner working of a sports show on network television. Like The Newsroom, but focused more on characters than on soapbox oration (to the betterment of the show, in my opinion), this Aaron Sorkin series was an often brilliant examination of relationships, politics, courage, and compromise that was tragically tossed aside because the public at large just didn't seem ready for it. That and Aaron Sorkin became sidetracked by another often brilliant show of his that was coming into fruition: The West Wing.
The Film: If you sit down and watch the show today (even just a few episodes), it's immediately evident that nothing about its ideas or characters is dated; if it aired right now, people would accept it with wide open arms. A film adaptation of Sports Night, encouraged and at least partially financed by a successful Kickstarter campaign (and I believe it would definitely be successful), would be the perfect antidote for modern box office schlock.