I'm going to wade in here: the point the parent was making is that the analogy is bad on purpose. It's not supposed to make sense. They don't want to say IE6 is like 9yo milk except in that old-age means things have deteriorated. They want it to appear that IE6 was an excellent browser but that it has somehow decayed.

Clearly they couldn't think of anything really good to say about IE8 except that it's not [that] old.

Perhaps they should have compared IE6 to MS Windows ME or something else from that time that was really really bad.

Maybe "you've ditched Billy Bass, you've moved on from The Sims, you're not wearing those capri pants anymore; no more monotonic ring-tones, ugg boots are out; you've served your time as Apprentice and made and lost your million on the 'net; you're not going to stand for no more snakes on no more planes; so, isn't it time you upgraded your broswer for what's left of this new millenium? - IE8 get it in FTW".

Bit formulaic, but that's my pitch - did I win?