The merits of the sideways-grip on a pistol are measured more accurately in terms of style and intimidation than mechanical. The people we see in movies who hold their pistols in this fashion are probably unconcerned with the maintenance of their firearm, and adds to the "nothing to loose" image.

An interesting gun catalogue i picked up in East Lyme, CT actually sold scopes and sights that attach to the side of the pistol, increasing accuracy in the sideways-grip. The advertisements, of course, point out that firing a pistol in this manner is "unadvisable".

Consider the shape of your crack dealer's average target. It tends to be a person and people tend to be alligned vertically when out on the street.

Consider the direction of movement of a handgun when it is held in the correct manner. It tends to tilt backward, moving the line of fire vertically upwards over your target. Gravity will then help to bring the gun down again, lining you up nicely for a second shot.

Now, if you want to look cool you might like to hold your gun sideways, but please be aware that any recoil will force your weapon away from your target and there will be no helpful universal force to bring it back. You had better hit the sucker first time if you want to look this stylish more than once.

All of the previous writeups on this subject only address the cosmetic appeal of shooting a gun sideways, as seen (as mentioned above by amnesiac) in John Woo films and gangster movies. These points are all valid; the gun is more likely to jam in this case, IF it is being fired right handed, in which case the ejection port, which is on the right side of the pistol, will be facing upward.

If, however, one is firing left handed, the ejection port will be facing downward and the possibility of jamming will be greatly diminished, perhaps even less than if the gun is fired in the traditional, zero degree alignment. Also, if firing a revolver, jamming is not an issue.

With that out of the way, we can address some tactical/functional reasons why you might actually want to fire this way. Note, since you will not be able to use the sights properly you should only use this technique at close range where you only need to point the gun in the general direction of your target- maybe fifteen feet or less. Point aiming, as the old gunslingers did it, can only be learned through practice so that the gun becomes an extension of your hand, and you know by feel where the bullet will go without having to use the sight posts. Practice makes perfect.

For one thing, the recoil of the gun will be absorbed by your pectoral muscle, instead of just the muscles of your triceps and frontal deltoid. Therefore the recoil will be marginally easier to control. And when firing a machine pistol, such as an Uzi, MAC 10 or Heckler & Koch MP5K, the recoil of the gun will propel it sideways in a vertical sweep. This is very useful for putting many bullets into a whole roomful of multiple assailants, a situation that calls for quick life or death thinking, and emphasizes gross motor skills over fine motor skills. Just make sure that you aim at the guy on the far right first, hold down the trigger, and let the recoil handle the sweep for you.

Also, when police or soldiers are firing form a tight squad formation, they might fire with their weapons turned sideways so that the hot brass cases are ejected downwards rather than into their buddy's shirt.

Initially, this method of firing a pistol or machine gun had absolutely nothing to do with accuracy, gunfight tactics, concerns over jamming, or the biomechanics of absorbing recoil. The business of holding a gun sideways was thought up while John Woo was shooting his action movies. Why? It was first done to keep actors and stuntmen from getting spent brass flung into their faces. Later, people kept doing it because they thought it looked cool.

If you've seen a John Woo movie, you know the actors fire off a whole lot of blanks, and their little metal casings get burning hot. On one set, Woo discovered that the particular gun models they had purchased for the movie were spitting spent shells upward. So, to minimize the chance he'd have to suspend filming indefinitely and take Chow Yun-Fat to the emergency room with a scorched eyeball, Woo just told him and the other actors to tilt the guns sideways so the brass ejected away from them.

Chow Yun-Fat looked like sex on a stick in those movies, so others (gangstas, American filmmakers, game designers) started copying him because he was so damn cool. Pretty soon, everybody was holding guns sideways purely to look like badasses, without any regard for whether or not it served any useful purpose.

In short, there's no sensible reason to hold a gun sideways unless you're shooting a movie on a budget and your props master happens to bring you poorly-designed firearms.

Reference: John Woo's commentary track on his DVDs "Hard Boiled", "The Killer", and "A Better Tomorrow".

There is one, and precisely one, area in which this has legitimate advantage: airsoft. In an airsoft war, if you have a spring pistol, holding it sideways allows you to cock and fire the pistol with extreme speed compared to other firing positions - in fact, almost equal to that of a low-quality electric gun.

This, unfortunately, corresponds to a likewise huge decrease in accuracy - but if you're only firing for speed, it's worth it.

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