Smith and Wesson M52...something kinda cool about an auto designed to feed .38 wadcutter.
Contenders are cool, sub MOA pistols that can whip up on a lot of rifles for bench rest accuracy.
The Smith and Wesson M3913NL. Not sure it's "cool" but it sure as hell is sexy!
Single action M1873 Colt, Ruger Single actions, FA single action....Just as cool as John Wayne himself.
Desert Eagle...Needs a butt stock, sorta like that Kel Tec thing mentioned above, but a real pistol in real handgun calibers.
NAA mini revolvers. If you can't see the cool in 'em, you just ain't cool, yourself.
The Smith and Wesson M10 will always and forever be cool, sort of in the 73 Colt coolness vein.
Smith 29...."The most powerful handgun ever made and can blow your head clean off. So you just gotta ask yourself, do I feel lucky? Well, do ya, PUNK!?" Or, my favorite. "We just can't let you walk outta here." "Who's we, sucka?" "Smith, and Wesson, and me." I mean, nuf said, right?