It doesn't bother me one bit. I'm a die hard H&R fan. I've seen all the toons on the site. I don't care if they throw an inside reference at me, because I know where it came from.
One of my favorates:

(Head explodes)

Woah the cheat! That computer has something against you! Did you ever like, pour Mountain Dew all over it?
Wow did I laugh.
If you're going to get someone into homestarrunner, have them I guess watch a few really good new toons, and then get them to start watching toons at the beggining of the compy era. Maybe show them a couple of the few good ones from back then though (halloweener, Vacation). I mean most of the compy emails are as funny as the ones today.
I can't see why anyone would be of not wanting to sit down and watch a bunch of old toons. Like it's almost the best entertainment in the world. I thought homestarrrunner.com was quite funny, What did I do? I spent hours watching every sbemail put on the site. I mean it's hardly a waste of time in comparrision to watching TV or playing videogames, and it's almost always more entertaining than watching either of them anyways.
An edit: I'd rather homestarrunner use inside jokes more than a TV show anyways, because if it's a TV show, you have to find a way to get your hands on all the earlier seasons. YOU HAVE TO PAY A BUNCHES OF MONEY to see them. Just so you understand the inside jokes. Homestar runner on the other hand is free, and would only take like, a day or two to watch everything.