It's for a World History course -- so not so much with movies set in America, I think? The Best Years of Our Lives is a GREAT movie though and everyone should watch it on its own merit.
My favourite historical film of all time is The Lion in Winter, but it may be too stagey and talky for this purpose. But oh, the dialog. The performances!
Gladiator sounds like a good bet. It's a decent movie with not super-violent action, interesting historical tidbits and a good character throughline.
Plenty of movies out there about the Tudors. Lots of Henry VIII stuff to choose from -- A Man for All Seasons and Anne of Thousand Days would be a good pairing for examining the same event from different perspectives.
Master and Commander - YES! While not featuring actual historical characters, it's got loads of fun details about Age of Sail Britain and it's just such an excellent film all around. I could see 15-year-old boys loving the film.
If he doesn't mind subtitled films, there is The Horseman on the Roof, which is very pretty to look at and has cool scenes about (an actual historical) cholera epidemic.
A couple of very good Australian War dramas set in early 1900's: Gallipoli and Breaker Morant.
After that, there are like a million WWII films. The Bridge on the River Kwai is on the top of that pile. I haven't seen that in ages but it's a fantastic film.
Not a movie, but: The Young Indiana Jones Chronicles? *ducking*
Thanks y'all that gives me several for him to choose from.
I don't know how much light Come See the Paradise would shed on the issue of WWII-era US internment of Japanese Americans, but it would at least raise the issue.
Also, Empire of the Sun would illustrate the Japanese occupation of Shanghai and the internment of foreign nationals.
I.E., there's more to human history than makes it into the textbooks.
Stalag 17 maybe? It's got humor and there's action. So maybe?
For WWII from a historical perspective, I'd go with The Longest Day over Private Ryan. It gives a fairly even handed treatment for all of the combantants, not just USA. Tora, Tora, Tora is similar for Pearl Harbor.
Why not just go with
Pearl Harbor
????
She wanted world history, not fantasy.
Also a bit grim, but it shows the aftermath of the bombs dropped on Hiroshima and Nagasaki, there's a Japanese film (subtitled in English) called August Rain. If it helps, it has Richard Gere in it.
Would he be too young, or too bored by, Band of Brothers? It covers a lot of WW2 european locations and battle conditions, for all that it's primarily a character study of the men of Easy Company.
Likewise, From the Earth to the Moon (1998--I have no input on more recent versions) is more recent history, but if you're doing The Right Stuff, the miniseries hits a lot of that time period, too.