Hurt Locker and Black Hawk down aren't mocking the war machine playfully, but they do a pretty good job of revealing the inhumanity and banality of it all.
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@chromeratt The movie War Machine was based on the Hastings book The Operators. It's not a full on mocking, but it exposes the asshattery prevalent in the general staff.
Someone else mentioned Pentagon Wars, which is also a good one.
@chromeratt The whole thing with Stripes was the testing of the combat Winnebago.
@chromeratt From the Strangelove era, The Mouse That Roared.