5. James Bond - Syphilis
I imagine 99% of readers probably saw this character prediction, rolled their eyes with a pronounced "Duh," and clicked the 'Next' button. For those brave few who stuck around to read my explanation, I'll try not to disappoint. James Bond, whether it's Sean Connery, Daniel Craig, or anyone in between, has been extraordinarily lucky in more ways than one (get it?). He's managed to survive the homicidal rampages of hat-wielding Asians, the metal teeth of the lumbering Jaws, a laser battle in outer space, and Madonna's Die Another Day theme song. However, he mostly did so by avoiding the problem. I think the outcome would've been a bit different if he had tried to feed Jaws or asked Oddjob to do a William Tell impression on him. That's essentially what he does with all women. It doesn't matter who she is, where he is, or how many bullets are presently flying at his head he must sleep with them. According to the Medical Institute for Sexual Health (at least, according to Google and other websites' attributions), there were really only two serious sexually-transmitted diseases prior to the 1960's: syphilis and gonorrhea. For that reason, I've settled on one of these two diseases as the most likely to strike Bond, even as he charms his way well into the 21st century. The sheer number of women he sleeps with just on camera increases his odds exponentially. And if there was any further doubt as to the likelihood, let's not forget that he sleeps with former sex slave Severine in his most recent outing, Skyfall. Because no one ever caught anything from a prostitute. No one.