They're hipsters. They embody what is hip, trendy, urban, cool - or at least, what they believe to be trendy. Their whole image is carefully-constructed to give you the impression that they simply don't care when they actually do care. Kind of like someone who spendds half an hour trying to make their hair look like they just woke up, and they fool no-one. They eschew what is popular and embrace counter-cultural icons, and they are often completely unaware of what those icons actually mean; for example, they'll wear a Che Guevara t-shirt without actually knowing who Che Guevara was or what he represented so they actually twist the image on itself. They value their individuality, but the irony of the way they group together is lost on them. They will likely get a tattoo of an Asian character of Native American symbol and claim it means "strength" or some such, and they will think they are the only ones with such a tattoo. They are the priveliged high school kids with an Ed Hardy "Born to Lose" tattoo (or, more likely, t-shirt because their parents won't let them get a tattoo). They are teenagers who never really grew out of the whole "the world doesn't understand me, but I understand the world" phase.
livemusic
Maybe it means a legendary challenge? They sure did achieve legendary results
That's quite an old joke btw, kind of weird to hear it again after so long. I do mean like a decade.
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