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Quite. Literally seems to be unique in this respect; if definition #2 completely undermines definition #1 what's the point in having that definition? I'll accept that context usually tells you which meaning is meant (like if it's coming from the mouth of a football pundit), but it still feels wrong.
PhilPub
bothwell
I grudgingly accept that this is becoming acceptable usage but it grates in a way that other words don't, because it renders the old usage useless - if "literally" can also mean figuratively, then we no longer have a word that means (old usage) literally. What do you say when you want to mean (with no doubt) actually what you're expressly said?