Colonel Joseph Ryan is a USAAC pilot who is shot down over Italy. He is taken to a POW camp, run by the cruel Major Basilio Battaglia. Ryan insists that Battaglia salute him as a superior officer, which is reluctantly translated by the sympathetic second-in-command, Captain Vittorio Oriani. The camp is mainly populated by British prisoners, along with a small number of American prisoners. The previous Allied commanding officer, who was British, has recently died, due to being placed in the "sweat box" as punishment for hitting Battaglia with a stick. When Ryan arrives in camp, Major Eric Fincham is the senior British officer. Ryan, being senior, assumes command.
Ryan, aware that the Allies are close to liberating Italy, reveals several of the prisoners' escape attempts, infuriating Fincham and the British soldiers. When Battaglia refuses to improve camp conditions, Ryan orders the prisoners to strip and burn their filthy clothes, forcing Battaglia to issue new ones. Battaglia throws Ryan into the sweat box as punishment.
After hearing of the Italian surrender, the guards flee. The British promptly put Battaglia on trial as a war criminal, and allow Oriani to defend him. Battaglia portrays himself as a broken man who has repudiated fascism. Ryan orders him to not be executed, but instead, to be put in the sweat box.
The men head out across the Italian countryside to freedom. Oriani moves forward in an attempt to contact Allied forces. In the morning, the Germans recapture the prisoners. Fincham thinks Oriani has betrayed them. When the POWs are put on a train, they find a severely battered Oriani in the prisoner carriage. They realise Battaglia betrayed them. The Germans shoot all the sick prisoners. Fincham blames Ryan for letting Battaglia live. The train travels to Rome, where a German officer, Major von Klemment, takes command.
Ryan uses a metal bar to pry up the floorboards of the car. That night, when the train stops, Ryan, Fincham, and Lieutenant Orde sneak out from underneath the train and kill several of the guards, then free a carload of POWs, who help them kill the remaining guards. Ryan and Fincham capture von Klemment and his mistress, Gabriella. As the train moves out, another train follows. Von Klemment reveals that the second train is carrying German troops and is on the same schedule. Further, von Klemment is to receive orders at each railway station. A German-speaking Allied chaplain, Captain Costanzo, is enlisted to impersonate the German commander to ensure their passage through the next station in Florence.
Through the documents received in Florence, they learn that both trains are headed towards Innsbruck, Austria. Through trickery, the prisoners switch their train onto a different line at Bologna. The troop train continues on toward Innsbruck. Von Klemment and Gabriella are kept bound and gagged, but Gabriella uses a shard of broken glass to sever their bonds. At a stop, von Klemment and Gabriella escape, killing Orde. Both are shot by Ryan.
Meanwhile, SS troops, led by Colonel Gortz, have discovered the ruse. The prisoners put the train on a siding, but discover that it leads to a German facility, which is subsequently bombed by Allied aircraft. The train races through, bombs exploding everywhere. Several cars catch fire, and several men are wounded. After they leave, the Italian engineer and Oriani disable the signals at one signal box, disabling the station's track displays and confusing the Germans. The prisoners then reroute the train to neutral Switzerland through manual switching.
Gortz and his troops pursue them. As the Alps appear, the prisoner train is attacked by German aircraft. Rocket fire causes boulders to fall and destroy a section of track. The POWs replace the damaged rail as the SS race up from behind. Ryan, Fincham, and others hold off the Germans, but many are killed in the battle. The prisoner train moves out as the men run for the rear platform with the Germans in pursuit. Fincham makes it and reaches back for Ryan's outstretched hand, but Ryan is gunned down by Gortz just as the train crosses into Switzerland.
The novel was published in 1963. The novelist David Westheimer had been a POW during World War II. He witnessed the bombing of Bolzano in 1943 from a box car. The New York Times book reviewer said the novel "has everything for the screen but the camera directions."
The novel was a best seller and film rights were bought by 20th Century Fox for a reported $125,000. The studio assigned Saul David to produce and Mark Robson to direct. Robson had intended to make The Centurians, but this was delayed when his chosen star, Anthony Quinn, was unavailable. Frank Sinatra had read the novel and wanted to buy the film rights himself; when he heard they had been lost to Fox, he offered his services for the lead role.
Von Ryan’s Express was a project keenly undertaken by 20th Century Fox, which was still financially reeling after the extravagance and critical bashing of Cleopatra. Fox, in a bid to prove that they were still able to make films on an epic scale, shot extensively on location in Europe and built a full-scale prison camp as opposed to shooting on a backlot. It was producer Saul David's first film for Fox. He followed it with Our Man Flint, Fantastic Voyage, and In Like Flint.
Rumours of a personality clash between star Frank Sinatra, who was flown by helicopter to the set, and director Mark Robson were not enough to cause problems as the film was shot with relatively little trouble. However, Sinatra did insist that the ending of the film be altered, ending any chance of a sequel. Sinatra also insisted the film be shot in Panavision rather than Fox's CinemaScope.
The film score was written by Jerry Goldsmith.
Von Ryan's Express achieved verisimilitude using aircraft, trains and wheeled vehicles photographed on location along with the occasional model. The fighters alluded to as Messerschmitts were indeed Messerschmitt Bf 108s. A majority of the film was shot on location around Northern Italy in Cortina d'Ampezzo and Firenze Santa Maria Novella railway station in Florence. The railway sequence at the film's conclusion, however, was shot in the Caminito del Rey walkway in the limestone gorge of El Chorro and in the adjacent railway bridge, near Málaga in Andalucía, Spain. Interiors were completed at 20th Century Fox Studios in Los Angeles, California. The POW camp (Campo Concentramento Prigioneri di Guerra 202) was also built in the front lot of the Studios.
Critics liked Von Ryan's Express. Variety noted, "Mark Robson has made realistic use of the actual Italian setting of the David Westheimer novel in garmenting his action in hard-hitting direction and sharply drawn performances." Frank Sinatra's daughter Nancy noted in her biography of her father that his performance fuelled speculation of another Academy Award nomination. Time Out London called the film a "ripping adventure" that was "directed with amused panache by Robson, and helped no end by a fine cast...", while the BBC's TV, film and radio listings magazine The Radio Times described it as "a rattlingly exciting Second World War escape adventure, with a well-cast Frank Sinatra..."
The film grossed $17,111,111 ($130,040,830 in 2016 consumer dollars) at the North American box office, equating to $7,700,000 ($58,518,374 in 2016 consumer dollars) taken in box office rentals. Variety ranked Von Ryan’s Express as the 10th-highest grossing film of 1965. Additionally, this was Sinatra’s highest grossing and biggest earning film of the decade.
The film was nominated for a Best Sound Editing (Walter Rossi) Academy Award in 1966, while the Motion Picture Sound Editors also nominated the film for Best Sound Editing in a Feature Film.
British Channel 4 ranked Von Ryan's Express number 89 on their list of 100 Greatest War Films, commenting, "A ripping yarn culminating in a wild train dash through [Italy], with director Mark Robson cranking up the tension and releasing it with some excellent action set-pieces." It has a 91% fresh rating on Rotten Tomatoes.