Alan is kind of a Dave Barry freak.  Seriously, we've got a full shelf devoted solely to the Barry and his words of wit and wisdom.  Besides Bill Cosby, Dave Barry is the only person on earth who can get Alan laughing until he stops breathing and I legitimately fear for his well-being.

Over the last two days of our clearly very spiritual Passover, while Alan and I were both fighting off nasty colds (his came complete with a mind-blowingly painful earache), we read through "Dave Barry in Cyberspace."  Written in 1996, its observations on the internet are antiquated to say the least (I don't know if "internet" and "America Online" were ever interchangeable terms, but they're definitely not now).  Nonetheless, it's pretty funny stuff.
While reading, we somehow got to talking about email addresses, and ranking the domains by relative coolness.  It seems to be deeply ingrained in both our heads that an email address @aol.com is lame, while @gmail.com is cool.  We both agreed that having a vanity domain, like say @stereosinai.com, is by far the coolest (unless it's a family domain - @smithfamily.net is pretty blah).  Where then fell into a heated argument about the relative merits of @yahoo.com, @hotmail.com, and some of the lesser-used domains.  Like I said, out Passover was way spiritual.

Where did this come from?  Do others feel this way?  What makes one email address cool, and the other worthy of hipster snubbing?

How would YOU rank the email addresses?