PJ Media has a post that lists “10 films that teach important lessons for leading in tough times.”
I think there are quite a few other movies and TV series that could be placed in this category. For starters:
Once an Eagle, which follows the comparative careers of Army officer Sam Damon–an excellent leader–and Courtney Massengale, an officer whose ambitions exceed his abilities and performance.
Friday Night Lights, focused on leadership in a sports, school, and community context.
The Caine Mutiny, which is indeed about leadership, albeit of a not very effective kind. “No one is totally useless, you can always serve as a bad example.”