Peruse the following movie list and go rent a few or dial 'em up on the Ancient Movie Channels. (And Band of Brothers isn't technically a movie, but it is, hands down, the best thing ever to have come from cable television.)
The first group is historically accurate movies [scale (HA) 10 = highest]:
These movies are of negligable historical accuracy but are all 10's on the cool scale and no kid could play army in my 'hood if they didn't know them well:
The Longest Day - Based on Cornelius Ryan's compilation of 1st-hand accounts, it features a platoon of marquee actors. Read. The. Book. Historical accuracy: 10.0
Band of Brothers - the history of Easy Company of the 101st Airborne from training, through D-Day, Norway, Bastogne and Berlin. It co-stars Peter, man from Office Space as Captain Nixon. I would've killed to have had a bit part in it. HA: 10.5
Patton - A riveting account of Ike's most notable general. My Old Man thought it an important enough film that he took me with him to see it. HA: 9.5
Ike: Countdown to D-Day - A&E did a great job of showing the delicate military and political maneuvers Eisenhower used to develop Operation Overlord. HA: 9.5
Midway - The Pacific Theater's all-star counterpart to The Longest Day (Henry Fonda and Robert Mitchum are double-dippers). HA: 9.5
Tora! Tora! Tora! - A clinical 360° view of December 7, 1941 from both sides, with subtitles (and Admiral Yamamoto's voice isn't the actor's). HA: 9.5
The Great Escape - A slightly stylised treatment of the prison break that lead to a brutal massacre of Allied POWs by the SS. And Steve McQueen has a motorcycle chase sequence because... because he's Steve McQueen, man. HA: 9.0
A Bridge Too Far - Another of Cornelius Ryan's compilations from the men who were there. It suffers from some fictionalized, and in my opinion, totally unnecessary social commentary-oriented sequences. I strongly recommend the book. HA: 8.0
The Bridge At Remagen - A bit narrowly focused and some hammy acting, but lots of firefight sequences that are easy to replicate in the yard. HA: 8.0
Twelve O'Clock High - Undeniably over-dramatic, but that can be forgiven since it was filmed about 6 years after it was set, AND the sacrifices made by the 8th Air Force are unquestionably some of the most heroic of the war and they get damn little credit for it these days. HA: 7.5
Memphis Belle - The most famous of the B-17s of the 8th Air Force is featured in a movie that's a bit overly sentimental and includes Harry Connick Jr. singing for some reason. It's on the list because I'm totally nuts for B-17s. HA: 7.0
Battle of the Bulge - This provides a passable history lesson about the Germans' last gasp in Europe, but I have a personal problem with the director's cavalier attitude for technical accuracy. They didn't even try to simulate Panzers or Tiger IIIs, using Walker Bulldogs (Korean era) for BOTH sides. HA: 6.5
There are a number of thinly-veiled chick flicks from back in the day, but they're set in the WWII period and are good family fare. If one needs basic history remediation, he might have to start with these:
In Harm's Way - Drama, but it's got the frikken DUKE in it, man. The Navy wins, Kirk Douglas' tragically flawed character redeems himself and the Admiral gets the pretty Nurse.
Mister Roberts - Fictional, but worthwhile for the story as well as showing the typical navy life aboard the many non-combat USN vessels. I Lie-berried this book.
Kelly's Heroes - What do enterprising GIs do in Europe on a 3 day pass? Steal German gold, what else? Ya hockey puck! And it stars Clint Eastwood. Must I twist your arm? Hell, I've memorized it.
The Dirty Dozen - Watch this movie, if for no other reason, to be able to appreciate Tom Hanks' biting sarcasm during Sleepless in Seattle when the women are crying over An Affair to Remember - you'll understand the pathos of James Brown's character in the final sequence. As an added bonus, Telly Savalas and Donald Sutherland are also in Kelly's Heroes.
Ambush Bay - Total fiction, but they have a cool mission that involves blowing stuff up. Mickey Rooney's final scene with the pineapples is classic and well-suited to imitate. Unfortunately, you aren't likely to find it anywhere. If you run across a tape or DVD of it, you have to tell me.
The Secret Invasion - This hard-to-find flick is arguably what The Dirty Dozen could be called a remake of, except Lee Marvin isn't likely to have agreed to play Stewart Granger's character. Mickey Rooney co-stars and he plays with grenades in this one too. Again, if you run across a copy of it - tell me.
Heaven Knows, Mr. Allison - Another sentimental favorite of mine. Robert Mitchum is CPL Allison, USMC, lost on a tiny island somewhere in the Pacific with only Deborah Kerr to keep him company. Just his luck, some Japs show up and they have to cohabitate in a cave. Oh, and she's a nun. I liked the story so much I ran down the long-out-of-print book in the Lieberry.
There's a whole bunch left of the list, some because I haven't watched 'em 20 or 30 times like these, and some because - durn, it's already a long list. You need more? I'll come up with more.
Operation Petticoat - Cary Grant takes command of the worst sub in the Pacific - the Sea Tiger. Because they get nothing but hind-teat leftovers, they have to mix the only paint they can scrounge - white and red - to cover the rusty barnacles and become infamous as a Pink Submarine and rescue some hot nurses. The Beatles had nothing on these guys with that whole yellow thing.
Father Goose - Cary Grant again. He's gets volunteered as a coast watcher for the Australian Navy, collects a French schoolmarm and the gaggle of little girls in her charge. She pronounces him a "Filthy Beast" and hides his whiskey. She gets bit by a snake (they think). The worried girls give up the whiskey. She gets snot-slingin' drunk and says silly things. They fall in love and get marriaged over the radio while the Japanese strafe the island. My wife just loves it, so I got it for her one Christmas.
Kiss Them For Me - This one stars Jayne Mansfield. !!! And Cary Grant, but he's hot for Suzy Parker. Navy officers on leave while their buddies fight on. They throw a big party in a San Francisco hotel. Hot wimmings everywhere, but their sense of duty prevails. It has Jayne Mansfield in it. She was way over the top, but somehow it worked for her.