Watch MoviestoWatch. Meet Hal, 87; Charlie, 87 and Maurie, 87. Three of a group of friends who gather every day at one p.m. in the village of Dorset, Vermont to play a game called "paddle tennis". They have been playing together for years. Moving beyond paddle tennis, The Longest Game takes on the 'game' of life, the stories we tell and the underlying forces that connect us all.