7. Wesker - Resident Evil 5
Throughout the series, Albert Wesker has made a name for himself as being the biggest baddest scenery chewer in the entire Resident Evil canon. He's so utterly cheesy and over the top but that just makes it all the more sobering when he utterly kicks your ass across the many boss fights he has.
That being said, Resident Evil 5 places him in a truly weird scenario, as in Chapter 5, you not only have to take on Wesker, but a brainwashed Jill in a battle that is both outstanding, and a little deflating if you manage to do well in it.
To better explain, Wesker states that he only has SEVEN minutes to play around with you before he has to get on with his busy schedule of being the best B-Movie Villain ever. Now to be fair, he's right to be cocky seeing as he can dodge your bullets and slide right on up to you in seconds before delivering a kick that would give regular humans an out of body experience, but it is possible to beat him.
Though some truly heroic tactics like shooting him in the back, and luring him into traps, you can down Wesker. However, in the next cutscene, he's all patched up, sauntering away like it was absolutely nothing. This leads Chris to fall into a trap leading to another boss fight with Jill.
You do get The Heart Of Africa treasure for your troubles, but still, bragging rights aren't as good as pieing off this smug tw*t.