Flynn and Reagan are Lt. Terrence Forbes and Flying Officer Johnny Hammond, two RAF officers (despite being Australian and American) who are serving on a bomber. Their bomber is shot down during a perilous mission to take out a bridge on the pre-war border with Poland. Forbes, Hammond, and the other three members of their crew are captured, but they make a daring escape from the office of Gestapo Major Otto Baumeister (Raymond Massey). And if that isn't cool enough, before they leave they manage to filch from Baumeister's office some sensitive documents regarding the location of Messerschmidt fighter plane factories. The Squad then makes a, well, desperate journey across Nazi Germany, while Baumeister tries to apprehend them.
Desperate Journey is typical of the kind of wartime propaganda films that Inglorious Basterds satirized. It's still one of the best films Ronald Reagan ever made, however, and could have been the big break that Reagan needed to leap to the Hollywood A-list...but Reagan got called up to serve in the Army, and his career never regained momentum. Flynn for his part failed his army physical (heart murmur and tuberculosis in one lung) and thus wound up fighting the war onscreen.
- Blood from the Mouth: Used to signal the deaths of the crewmembers who don't make it out of the crashed bomber, as well as for the captain, who dies of his wounds shortly after they escape the plane.
- Ceiling Cling: The guys do this by clinging to the understructure of a bridge, in order to surprise some German sentries. Justified as the sentries are distracted by their comrade, who is at the bottom of a ravine moaning from the Tap on the Head that he received from our heroes.
- Celebrity Paradox: "Why do you have to wake me up every time I've got a date with Ann Sheridan?", says Hammond after he's roused from sleep. Ronald Reagan had starred with Sheridan twice, including the film he made before this one, Kings Row.
- Contrived Coincidence: If you are a desperate bunch of airmen, cowering in an alley while one of your guys is bleeding out from a bullet wound following an ill-advised raid, you run the risk of people walking by the alley and seeing you. It's good if the person that walks by the alley and sees you is not only an anti-Nazi, but a member of the anti-Nazi underground able to get you both safe refuge and medical care.
- Five-Man Band:
- The Leader: Forbes, exceedingly cool and confident, instantly taking charge after the crash and deciding on what course of action to take (for better or worse).
- The Lancer / The Smart Guy: Hammond and Forrest each flip-flop between these roles. Hammond is very similar to Forbes in terms of temperament and goals, acts as his right-hand man for the most part and is very technically proficient and capable of working out how to turn potentially hopeless situations to his advantage; while Forrest is more reserved and regularly questions Forbes' judgement (but always agrees that Forbes is the leader, even immediately turning down the opportunity to take that title for himself when Forbes angrily confronts him about it), constantly trying to rein in his comrades' more ambitious schemes and is always focusing on the bigger picture.
- The Big Guy: Edwards, the oldest and most boisterous of the group.
- The Chick: Hollis, sustaining injuries when the plane initially crashes and at one point attempts to give himself since he's afraid of preventing the others from getting home safely.
- Hiding Behind the Language Barrier: One instance of Baumeister taking with his dragon in English is excused by Baumeister not wanting a German private to know what they're talking about.
- High-Class Glass: Naturally, Baumeister the evil Gestapo officer sports one.
- Instant Messenger Pigeon: A Polish saboteur gets shot, but not before he dispatches his homing pigeon to let the RAF know that he just dynamited a bridge. How the saboteur got a pigeon to send back to England is not explained.
- I Will Only Slow You Down: Hollis, injured from the plane crash, attempts to sneak away so as not to slow his comrades down. The others bring him back.
- La Résistance: The film opens with a Polish partisan blowing up a bridge. Later, the squad has the great good luck to run into a woman who is an anti-Nazi and a member of the German resistance.
- New Meat: Hollis, son of an RAF flying ace from World War I, newly assigned to a bomber out of training. He shoots down one German fighter before they crash.
- Riding into the Sunset: Or flying into the sunset, as the film ends with the German plane that the gang stole flying off into the sun.
- Soft Glass: Forbes flings himself through a window when he sees that a couple of German guards have the drop on the rest of his men. He gets up without a scratch.
- The Squad: Forbes is the dashing leader, Hammond is The Lancer and resident Deadpan Snarker, Sgt. Edwards is The Scrounger, Officer Forrest is The Cynic who tends to cast doubt on Forbes's decisions, and Hollis is the New Meat.
- Switch to English: All the Germans speak German, but in one scene the movie needed to get some plot across, so Baumeister asks his subordinate "You speak English, don't you?", followed by the rest of the scene being in English for no damn reason at all.
- Techno Babble: Probably the highlight of the movie comes when Baumeister is trying to get Hammond to share classified info on how RAF engines work. Hammond unleashes some epic technobabble."There's three things you gotta understand. As I said before, the daligonitor is amfilated by the thermotrockle. It's made by its connection with the franicoupling of dernadyne. Even at cruising speed the kinutaspel hepulace is prenulated by the amsometer."
- Throw-Away Guns: Played straight when Forbes flings his pistol at the German factory guards after running out of ammo.
- Travel Montage: The squad does stuff like hide in a hay cart and steal a car, all while the typical line-across-a-map monitors their progress.