I was definitely a bit of an elitist dick. I've mellowed out so much since those days, and I embrace that kind of music I used to eschew back in the day more than probably anyone else on these boards these days.

Aside from the whole OkayPlayer/Rawkus/DefJux/Anticon stuff, the people that knew of stuff like Erule's "Listen Up" were the real heads.
https://youtu.be/wgf_ujr5XrE

There were also some artists and songs that felt like they were particular to these boards (more popular than on other backpacker-centric sites). Like we had some people that really rode for The Nonce on here. And certain remixes were widely revered (Pete Rock's remix of PE's "Shut 'Em Down," the remix of Black Moon's "Buck 'Em Down," etc.).

Other's that come to mind:
Boogiemonsters - Honeydips in Gotham: https://youtu.be/MCz3wsFP9d8
Heltah Skeltah - Leflaur Leflah Eshkoshka: https://youtu.be/2ATIiauFbZI
Channel Live - Mad Izm: https://youtu.be/Nbzz9T4KeLM
Souls of Mischief - Cab Fare: https://youtu.be/pIOM8mCS1fk
DJ Krush - Meiso (feat. Black Thought) (DJ Shadow Remix): https://youtu.be/UR0AfZoWVFk
Mountain Brothers - Galaxies and Paperchase: https://youtu.be/Ptd2CuBR-Tg
https://youtu.be/zUi7VnZW6XQ