Charlie Wilson's War (2007)

Danger Level: 5

In this 2007 movie, Tom Hanks plays a U.S. Senator who begins funneling money and weapons to the mujahadeen fighters in Afghanistan in order to assist them in their fight against the Soviets.  It was an intricate plot which involves dummy corporations, channeling the weapons through third parties and friendly nations (and unfriendly nations), and getting the weapons into the right hands.

 There was about a million things that could go wrong, but miraculously, the plan worked.  (At least, until the Afghan freedom fighters later turned against their American benefactors in later years!)

Click here for the Best and Worst Afghanistan War Movies.

Saving Private Ryan (1988)

Danger Level: 6

Tom Hanks and his platoon are tasked with going deep into enemy occupied France to find a single soldier and return him home to his mother (his mother having lost all of her other sons to the war.)  The territory they have to transverse is thick with Germans and quite dangerous.  It could almost be considered as a suicide mission in order to retrieve a single man, which is why it ranked on this list of the top covert missions of all time.

Click here for the War Dream Team.

Argos (2012)

Danger Level: 6

Ben Affleck has to enter Iran during the height of the Iranian Revolution (where Iranians are acting crazy, offering up mob justice, and generally being quite radical) and pose as a filmmaker, in order to extricate a number of American embassy workers who have taken refuge at the Canadian Ambassador's house after the siege of the American embassy.  If they are caught, it would most certainly mean their deaths, as well as a huge embarrassment for the Carter administration.

 Of course, there are slight difficulties involved - namely, having embassy employees learn to act overnight, memorize reams of fake details about their new identities, and manage to relay this information about themselves convincingly to airport customs agents.  (This mission happened to be successful, but the Carter administration would be embarrassed in other ways when the commando raid to rescue the diplomats being held hostage ended up going horribly wrong.)

Click here for the Top Academy Award Winning War Films.

Inglorious Basterds (2009)

Danger Level:  7

The Basterds, led by Brad Pitt's Aldo Raines, drop into Nazi-occupied France, ahead of the U.S. invasion, and dressed as civilians they are each tasked with bringing back 100 Nazi scalps.  A small, un-supported commando unit, they're tasked with dealing death and destruction to the Nazi regime.  They're not entirely without mercy though, they always leave one alive, so that he can tell others what they've done, thereby allowing the legend of the basterds to grow.

 (This last Nazi that's left alive is giving a parting gift:  A swastika carved into his forehead with a knife, so that for the rest of his days on Earth, he will be recognized as a Nazi.)  Deep in enemy territory without support or re-supply...sounds pretty dangerous, enough to be on this list, anyway.

Click here for the Best and Worst Nazi War Movies.

Lone Survivor (2013)

Danger Level: 8

In Lone Survivor, a small team of four Navy SEALs is sent by themselves deep into the wilds of Afghanistan to assassinate a high ranking Taliban figure surrounded by hundreds of fighters.  What they hope to do is to take out their target, and they disappear into the surrounding mountains and never be seen.  What could happen is that their location could be identified and they could be attacked by the hundreds of fighters who would end up facing off against what is ultimately just four men.

 And given that a movie was made about this, everyone known how things turned out. 

Guns of Navarone (1961)

Danger Level:  9

A small commando unit is tasked with destroying large Axis guns that are preventing the movement of thousands of Allied troops.  This small unit, led by Gregory Peck first must cross the Aegean Sea disguised as fisherman, they are boarded by Nazis (whom they kill), they wreck their boat, end up scaling cliffs, to finally arrive at a small mountain hamlet, where - you guessed it! - they have to kill more Nazis.

Click here for the Best and Worst Special Forces War Movies.

Zero Dark Thirty (2012)

Danger Level: 10

It doesn't get much more dangerous than this:  Navy SEALs secretly enter Pakistan.  And not just anywhere in Pakistan, but just a mile from a Pakistani military academy.  Threats include being captured by the Pakistani military, having their aircraft picked up by radar on the way into the country, oh yes, and having to still takedown a heavily secured compound, with an unknown number of armed fighters inside.

 If they failed, it would be considered one of the most disastrous military missions of all time, and likely would have brought down the Obama Presidency.

Click here for the Best and Worst War Movies about 9/11.

Where Eagles Dare (1968)

Danger Level:  10

Clint Eastwood has a slightly difficult task:  Infiltrate a Nazi lair, and rescue an American General from a heavily fortified Nazi castle.  That's all.  No big deal.  Classic American war movie where the Nazis speak perfect English for the benefit of the American audience (as well as Eastwood and his fellow soldiers who were sent to infiltrate.)

Danger Level: 10

Nicolas Cage and Sean Connery have a simple task:  Going underwater, come up through the sewer systems in Alcatraz, which has been seized by a rogue Marine Recon Force, take out the Marines, rescue the hostages, and stop the Marines from launching missiles tipped with chemical weapons at the San Francisco civilian population.  No big deal.

Danger Level: 10

Lee Marvin is tasked with infiltrating German occupied territory and assassinating a number f high ranking officers.  The kicker though is that instead of a well trained squad of American commandos, he's instead given some of the worst felons and prisoners the American penal system has to offer.  In exchange for their service, their sentences will be reduced.  So it's not just undertaking a very dangerous mission with a low probability of success, it's undertaking a very dangerous mission with a low probability of success, while being in charge of rapists, murderers, and other felons.