The Man Who Would Be King
Sean Connery made only three really great movies in his life: Robin and Marian, The Wind and the Lion, and The Man Who Would Be King. All three came out in 1975 and 1976. (The first four Bond movies are culturally iconic, but they were really more cool than great.)
The Man Who Would Be King is on at 8PM on TCM this evening. It's based on the story by Rudyard Kipling. Kipling was certainly not politically correct by today's standards, and the movie cleaves fairly closely to the story. But Kipling also deals skillfully with timeless notions like courage, ingenuity, ego, and hubris, which resonate in any era.
By 1975, Connery was no longer the young panther he was in the early Bond movies, but he still looked great, and he was perfect in the role of an adventurer whose ego gets the better of him. (Later in his career he was cast as a wise man several times, but he was never convincing in those roles.) Connery's romantic interest was played by Shakira Caine, the wife of his co-star Michael.
At 10PM, you can turn to FX and watch Justified, another great boys' adventure story. This one was created by Elmore Leonard, who deals with similar timeless themes.
So people should still be enjoying him in another hundred years as well.