First, we'll clear up a few misconceptions about Leon, with two pictures that sum up the general casual fandom opinion of him.
This is not what Leon really is, at least on a regular basis. He can be cool and suave, but the excessively shojo way he's drawn and general feeling? Ehh, a little extreme. (Not dissing the art, it's beautiful. Just making a point.)
As for the second one, the game might have been that easy for you, the player, on your third run through with the infinite-ammo Chicago Typewriter, tactical vest, and Ashley in a suit of armor. But for Leon? There's no way. He has no clue what's coming, and isn't shown in cutscenes to have anything but a handgun and possibly a shotgun. Think your first playthrough when you were twelve. I imagine he spent most of the time trying really hard not to die. So basically, he's more like:
Now on to some of my favorite pictures in no particular order.
All four (canon) character designs, for your convenience.
The triadic color scheme. Do you see it yet?
Because you know Ashley fell asleep two minutes after she got on that jet-skii, and Leon had to carry her off of it onto the rescue chopper. Or he could have woken her up and made her walk, but he's not that mean.
Raw fish killed with a handgun are a prime source of nutrition, and even heal cuts!
Why Leon doesn't smoke.
Some days, working for the Secret Service can be really boring.
DO NOT WANT.
"What the hell, Ada? That was my nice jacket and you shot a hole in it?!" "No, I shot a hole in the Ganado wearing it."