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"War is a criminal enterprise. I fight it with criminals."
Colonel Masters
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Play Dirty is a 1969 war film by Andre DeToth (his last film in fact), starring Michael Caine, Harry Andrews, and Nigel Green, and Nigel Davenport.

The film is set during the North African Campaign in World War II. After several failed missions in German-held territory, Col. Masters (Nigel Green) wins a reprieve from the double-dealing Brigadier General Blore (Harry Andrews) by offering to destroy a Nazi fuel dump way behind the battle lines. Masters sends out a seven-man patrol headed by the mercenary Captain Cyril Leech (Davenport) but technically commanded by Captain Douglas (Caine), an oil supply officer previously attached to rearward duties. The twist: Every man in this patrol is a convicted criminal.

Released during the Vietnam War, the film is an extraordinarily cynical deconstruction of Elites Are More Glamorous, highlighting both the brutal behavior that's necessary to survive behind enemy lines and how little loyalty and ethics factor into special ops strategy. The patrol start out as Villain Protagonists and get worse as they go, with the biggest threat not being the Nazis but each other - and their unethical, self-serving commanders back at HQ who double-cross them at every opportunity

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The film was a financial failure, with many at the time suggesting that its bleak tone and Black And Black Morality is inappropriate for a movie set in World War II (which had decidedly clear-cut bad guys), while others myopically dismissed it as a ripoff of The Dirty Dozen (released a year earlier). Years after release it earned something of a cult following thanks to high profile advocates of the film like Martin Scorsese (who included it on a long list of guilty pleasures for the May-June 1998 issue of Film Comment).

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This work features examples of:

  • Attempted Rape: The commandos kidnap a German nurse to care for one of their wounded, and attempt to rape her as soon as the officers' backs are turned. Her patient intervenes by shooting one of her attackers in the ass.
  • Bad Boss: Blore approves Masters' plan to have his commandos blow the fuel dump,and then immediately turns around and assigns the same mission to his own officer, taking credit for the whole idea and using Masters’ exact same words. Blore then dispatches a second, official Army unit with the exact same mission, hoping Leech and Douglas's group will be killed serving as decoys for the ‘official’ strike force.
    • Later, Blore informs Masters that the Allies are rolling through the country and that High Command now wants the fuel dump intact. Masters decides getting in contact with the commandos will be too difficult, and instead leaks to the Germans their plans and whereabouts.
  • Black And Black Morality: One side is a group of mass-murdering sociopaths. The other side are Nazis. The battlefield is presented as a place where moral and ethical rules simply don't exist, which is fairly unusual for a movie set in WWII.
  • Cruel Twist Ending: The Allies have broken through German lines and are sweeping through the desert - and the fuel dump that needed to be destroyed becomes a crucial objective to be captured. Since headquarters is cut off from the commandos, they tip off the Germans about the impending attack, which ends with everyone but Leech and Douglas killed. The captains flee to nearby Benghazi when the British Army breaks through. Still wearing the German uniforms they’d use to infiltrate enemy lines, the two concoct a white flag of surrender and march out to greet the liberators - and promptly get gunned down by a trigger-happy Tommy.
    British Soldier: "Sorry sir, I didn’t see the white flag.”
  • Crossing the Desert: Most of the movie is this trope and the practical problems that ensue. The ground is so rocky that their tires wear out alarmingly fast, and they’re constantly stopping to change them. Strung out 400 miles behind enemy lines, the mini-convoy encounters unexpected minefields, and clever German booby traps. One of the most famous scenes is an almost Hitchcockian sequence of them simply trying to haul three jeeps up a cliff.
  • Curb-Stomp Battle: In a largely successful attempt to avert Do Not Do This Cool Thing, all of the battles are brief and abrupt steamrolls where one side can do little more than run around in confusion and horror while getting massacred by another, often unseen force.
  • Dressing as the Enemy: The commandos carry uniforms of three armies and tune to American, German and Italian radio stations every time they change identities. This backfires a few times throughout the movie, especially at the ending where the survivors of the group get mistaken for Germans and shot by their own men.
  • Dropped a Bridge on Him: Everybody in the squad meet abrupt, unceremonious ends.
  • Elites Are More Glamorous: Averted. The commandos don uniforms of the enemy, loot corpses, revel in insubordination, accept bribes to bring back officers alive,(nearly) rape a German nurse, kill innocent bystanders and otherwise commit egregious and unclean deeds in the name of 'the mission.' What success they have has little do with their combat skills and everything to do with their willingness to "play dirty," and the one time they meet actual resistance sees them getting massacred.
  • Fakin' MacGuffin: The fuel dump the commandos are after turns out to be a decoy.
  • General Failure: The commanding officers aren't incompetent so much as viciously apathetic and self-serving, and treat the chain of command as a license to squander the lives of anybody below their rank.
  • Females Are More Innocent: The captured female nurse is the film's only sympathetic character.
  • Hope Spot: After the disastrous attack on the fuel dump, one of the commandos tries to flee by crawling through barbed wire, only to find himself staring at a machine gun. After a moment of horror, the German breaks into a smile and lets the relieved irregular crawl a few more feet before blowing him away.
  • Karmic Death: The commandos spend the film killing non-combatants, and themselves get unceremoniously gunned down while fleeing or surrendering.
  • Kill 'Em All: The entire squad and the captive nurse are all dead by the end of the movie. The only person who might still be alive is critically wounded to the point where his demise is only a matter of time.
  • Mindlink Mates: In a rather bizarre moment, the wounded Arab guide shoots the German nurse after his homosexual lover is gunned down in the climax, suggesting they have this.
  • Naïve Newcomer: Douglas isn't as idealistic as most examples, but he still holds some pride in his uniform and has some notions of "fair play" when we're introduced to him. His subordinates openly defy him, and his superiors take advantage of this naivete to backstab him at every opportunity.
  • Obligatory War-Crime Scene: The movie delights in demolishing the old-movie notions concerning the ‘rules’ of warfare. The irregulars execute medics and rape prisoners. The Germans, for their part, are also pretty happy to gun down fleeing and surrendering soldiers, and the brief glimpse we have of the British Army is of them gunning down surrendering Germans (actually Leech and Douglas) and claiming that they "didn't see the white flag."
  • The Peter Principle: Douglas is actually an oil company engineer loaned to the Army to work only in fuel transfers and has no actual military experience, not that this saves him from getting impressed to lead a suicide mission. While he does make a vital engineering contribution to the mission, his subordinates openly laugh at his efforts at command.
  • "Shaggy Dog" Story: When the irregulars find the ammo dump in question, it's revealed to have been a decoy (complete with straw statues as "guards"). They head to Benghazi and find that the real ammo dump is there, and decide to blow it up as a distraction while they steal a boat and flee. Which leads to . . .
    • Shoot the Shaggy Dog: They end up tripping an alarm at the real dump and only manage to do minor damage in the ensuing chaos, which results in the deaths of everybody but Leech and Douglas. Then it's revealed that they made it to the dump less than a day before the actual British army, rendering the entire mission pointless.
  • Shoot the Medic First: Finding themselves out of a car, the crew ambush a German ambulance, kill the medics, and kidnap the nurse.
  • Sliding Scale of Idealism vs. Cynicism: Very much on the cynical end.
  • So Much for Stealth: Leech "forgets" to unload one of the trucks they're towing up a cliff, and the weight causes the cable to snap and the truck crashes to the ground, alerting the Germans to their presence. (Un)Fortunately, Blore's "official" strike force happens to be in the area and takes the heat for it, leaving the irregulars unnoticed.
  • Source Music: The film opens to a German officer driving to the tune of Lilly Marlene. The music suddenly changes to a swinging British version of the song, and he changes his Afrika Korp headgear accordingly to a British peaked cap.
  • Suicide Mission: A very literal example, as the irregulars aren't actually expected to succeed, but they serve as a decoy for a much larger regular force. Ironically, it's the regulars who drive into a German ambush and get killed, serving as the decoys for the decoys.
  • Unfriendly Fire: It's implied that Leech murders every officer sent into the field with him. He later admits that his interest in Douglas's survival is because Masters offered him 2,000 pounds if Douglas survives.
  • War Is Hell: And bleak and amoral.
  • Would Hit a Girl: The only reason Leech doesn't execute the unfortunate German nurse on the spot is because one of his troops is wounded and needs treatment. She ends up suffering a lot of abuse, and gets executed at the end anyways.
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