What is up with everyone using the vague general context of the words "Winning" and "Losing"?

Is it just a new fad slang way of saying bad and good? Like when we used to say, "Dope" or "Gnarly" or more recently "Amazing" and "Fail"? LOL...I guess if i have to ask then i really am getting OLD! Anyway i've noticed it in blogs a lot and am curious. If anyone can approximate the origins (time,place) of this meme, that would be....."WINNING"!