It’s not really a trilogy but I suggest watching (1) Darkest Hour, (2) Dunkirk, and (3) Their Finest all together (in that order).
If history isn’t your cup of tea…how about a trilogy with Jeff Bridges? Try (1) TRON: Legacy, (2) Seabiscuit, and (3) Tucker: The Man and His Dream. They may seem unrelated, but I’m working under the precept that, “everything ever is connected.”
“This is not the finish line, my friends. This is the start of the race. The future is the finish line!” — Charles Howard