Von Ryan's Express

Von Ryan's Express is a 1965 World War II adventure film starring Frank Sinatra and Trevor Howard, based on a novel by David Westheimer.

Colonel Joseph L. Ryan (Sinatra), an American pilot, is shot down in Fascist Italy and put in a Fascist prisoner of war camp there, where he becomes the new ranking officer among the Allied prisoners. He's nicknamed 'Von Ryan' by the mainly British prisoners for his initial concessions to the jailers, spoiling previous escape preparations in order to improve current conditions for the prisoners. Despite proving that he's willing to both push their jailers and suffer for his beliefs, the name catches on when Ryan sparing the life of the camp commander in the wake of the Italian surrender leads to the POWs being recaptured by the Germans, who load the survivors on a train headed for a German camp. In the shadow of the Italian Alps, Ryan and the British POWs take control of the train; trapped behind enemy lines, their only option is to pretend to still be under German control and avoid suspicion while heading for neutral Switzerland. But it's not long until the Germans are in hot pursuit.

While making the film Sinatra met his future wife Mia Farrow(29 years his junior), who was shooting the TV show Payton Place on the same lot.

Tropes used in Von Ryan's Express include:

Appropriated Appellation: "Von Ryan", which changes from an insult to a nickname through the film.
The Big Board: A German diagram showing the status of their railroad system.
Bittersweet Ending: The train makes it into neutral Switzerland, but Ryan and half the speaking cast die fighting the waves of Nazis approaching the final bridge.

Fincham: (final lines) I once told you Ryan, if only one gets out, it's a victory...

Captain Smooth and Sergeant Rough: Ryan and Fincham. Ryan is a self-declared "90 Day Wonder" who was drafted in to serve as an Army pilot, earning his rank of colonel due to age and education. Fincham is a major but has lived his whole life as a battlefield soldier, and obsesses over discipline and adhering to a code of behavior that Ryan can't fathom. They clash early and often over every step Ryan implements, with Ryan proved right some times and Fincham proved right (painfully so) at other times.
Dirty Business: What war is for people like Fincham. He's able - and more than willing - to do a lot of the nasty stuff Ryan can't even think of.
Face Heel Turn: The prison camp's second-in-command Capt. Oriani. His eyepatch suggests he was an Italian who's actually faced battle, and is openly courteous to the Allied prisoners. When Mussolini falls and the prisoners seize control of the camp, he switches sides and offers to help the POWs escape despite Fincham's concerns. He does.
Fascist Italy
Great Escape
The Hero Dies
Hold the Line
Honor Before Reason: Ryan shows up with a camp divided between American and British POWs. It's because Fincham insists on constant attempts to tunnel out of the camp (and is hoarding much-needed medical supplies for those attempts). Ryan, knowing that the Allies are landing in Italy as they speak and that real freedom is weeks if not days away, uses his rank to overrule Fincham.
Karma Houdini: The corrupt Major Battaglia. He suffers some public humiliation and a few hours in the hot box for maltreating the prisoners, but he's fat and happy after being rescued by the Germans.
The Lancer: Fincham. He doesn't like it. Until Ryan dies at the end.
Naked People Are Funny: When Ryan orders the entire camp of men to strip and burn their clothes to force the corrupt commandant Battaglia to issue fresh clothes he'd been hoarding for the black market. Borders on Fan Disservice considering how many guys just don't work on their tan lines...
Playing Against Type: This was the first role Sinatra had that didn't ask him to sing.
Prison Ship: Actually a train.
Shoot the Dog: Ryan killing the German commander's mistress to keep her from alerting the Germans.
- The Germans recapturing the escaping POWs shoot the sick prisoners rather than treat them.
Smug Snake: Major Battaglia.
Those Wacky Nazis: Not so wacky in this movie. They're brutal in this film.
Title Drop: The novel had one at the end -- Ryan makes it across the border, and laughs to discover someone painted "Von Ryan's Express" on the side of the train.
World War II
Would Hit a Girl: Ryan. This was part of the reason Sinatra insisted on Ryan dying at the end.