After spending a lot of time recently on Beefheart's music, I would definitely start with Clear Spot. I actually think his latter-day material is pretty good, too. Shiny Beast (Bat Chain Puller), Doc at the Radar Station, and Ice Cream for Crow are all great. The music seems more polished but still has all the complex band interaction in the background. I may have to dive into TMR again. I did like Lick My Decals Off, Baby. I think Van Vliet said this was his favorite album.
It's definitley music that you have to spend some time with and I think the people that allowed Van Vliet's music to come to life (Drumbo, Harkelroad, etc.) deserve a LOT of credit.
I usually direct people to Clearspot as a decent starting point. Slightly more accessible, yet still gives you a taste of the Beefheart vibe.
This is probably old news, but I just discovered this really good introduction to TMR.
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