Bill O'Reilly was successfully talking over a rapper (because rappers are actually about being coherently heard, while Bill doesn't suffer that limitation) when Cam'ron dropped two syllables to destroy his target more completely than an A bomb. Bill was shut down so hard that he had to go to his internal happy place, which at that exact moment must have looked like a Klan-staffed Bioshock.
Unfortunately this became a meme, which is a great way to undo the good of anything. Now it means "LOLZOR, Look at t3h little nooblet."
What They're Actually Saying
"Umad?" exists for the same reason as warning symbols: A noxious danger has become so prevalent, the entire culture now instantly recognizes it as bad.
Original trollface by Whynne
It's the awful online idea that pissing people off is a victory in its own right. Honestly, when the Internet becomes sentient and starts attacking us, it'll only be because it thinks we like it. "Umad?" elevates this to the level of zen paradox, pissing people off by implying that they're pissed off, and just like zen monks, the only solutions are to stop thinking or use violent kung fu. Note: Kung fu doesn't work online.
"Umad?" should be useful, because mocking people who try to kung fu their rage through a keyboard is more natural than drowning when you try to breathe in a septic tank. And they're very similar experiences. Jumping in when you're angry is an unpleasant mistake, and you really should have known better. A keyboard isn't a conversation. There's no need to do something you regret in the heat of the moment.
In the long term, this is less damaging than using the Internet angry.
But "umad?" now ends the discussion by dismissing any contrary argument as childish rage. Disagree with them? U mad! End of story, because when someone uses a meme instead of logic, they don't like the latter. Memes are voluntary brain damage, short-circuiting higher thought processes with copy and paste, because these people view thinking as unpleasant homework and they'd rather copy it off the Internet. They've become a vehicle for regurgitating things they've seen before, the textual equivalent of the winter vomiting bug. And about as fun to spend time with.
What They Think They're Saying
That they just showed that bitch. Probably a feminist. Amirite?
What They're Actually Saying
There are websites for people sexually attracted to dogs, filtered by breed and gender, and they come off looking better when they use the word "bitch." They violate man's best friendship and they're still more sympathetic than people who insult half the human population. When you define someone's worth by "gonad dangling," you don't understand the former or use the latter. Unless you're discussing the pain of being kicked in happyplums hammock, gender isn't relevant, and if you use the word "bitch," you're on course to becoming a specialist in that subject.
The insult "asshole" criticizes them for spewing shit, "moron" for being an idiot, "bitch" for being female. It's at this point where people will complain about humor, satire, valid uses of the word and a sack of other things that simply aren't relevant when it's KratosWarBoner69 screaming at a girl playing Street Fighter. Using the word "bitch" reverses the polarity of a comment: If someones hates you by using the word "bitch," you're probably moving in the right direction. It's a better moral compass than a Morgan Freeman character. And if you can't imagine Morgan Freeman reading a comment, you shouldn't do it either.
Luke has a website, tumbles and responds to every single tweet.
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Check out more of Luke on Cracked in The 7 Most Impressive (And Depressing) Geek Collections and 7 Scientific Ways Coffee Gives You Superpowers.