Damn y'all, this is why I've had trouble finding a starting point, 3 of you who gave answers all listed different albums

DL'd "How I Got Over" and giving it a spin, keep them suggestions coming tho
The responses you're gonna get are all basically gonna be personal preference.
Illadelph is generally considered their best album, Things Fall Apart was their breakthrough album, and outside of The Tipping Point all of them have wide critical acclaim.
Can't really go wrong with any of them IMO. I'd start and just listen to them in order.
Piff on every album:
[ame=http://www.youtube.com/watch?v=9lpujDkJWs8]The Roots - Guns are drawn [HD] - YouTube[/ame]
Even off-tracks here and there are awesome:
[ame="http://soundcloud.com/jelofanticon/02-zen-approach"]Zen Approach by jelofanticon on SoundCloud - Hear the worldâs sounds[/ame]
[ame="http://www.youtube.com/watch?v=Ig5bGIrJW3o"]DJ Krush & The Roots - Meiso (Da Beatminerz Remix) - YouTube[/ame]
and this is the track that solidified Black Thought as a GOAT-quality emcee for me:
[ame="http://www.youtube.com/watch?v=NhM2HTs0QVY"]The Roots Silent Treatment (Da Beatminerz Mix) - YouTube[/ame]