The Last Detail a 1973 comedy-drama staring Jack Nicholson. The film was nominated for three Academy Awards.
U.S Navy petty officers 1st class Billy "Badass" Buddusky (Jack Nicholson) and Richard "Mule" Mulhall (Otis Young), are awaiting orders in Norfolk Virginia when they are assigned a shore patrol detail escorting young sailor Larry Meadows (Randy Quaid) to Portsmouth Naval Prison near Portsmouth New Hampshire. Meadows has drawn a stiff eight-year sentence for the petty crime of trying to steal $40 from a collection box of his C.O.'s wife's favorite charity. Despite their initial resentment of the detail, the likeable Meadows begins to grow on the two Navy "lifers" as they escort him on a train ride through the wintry north-eastern states; particularly as they know what the Marine guards are like at Portsmouth and the grim reality facing their young prisoner. As the pair begin to feel sorry for Meadows and the youthful experiences he will lose being incarcerated, they decide to show him a good time before delivering him to the authorities.
The movie was reminiscent of when I was stationed in Germany with the U.S. Army and drew a similar type detail.