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Where should I start with his back catalogue?
but if you can't get into it straight away (many can't), the other stock answer is Safe As Milk.
Ultimately, two very different albums though.
Kandy Korn, seriously.
Don't start with Trout Mask Replica. It's great but as an intro to Beefheart it might twist your melon a little.
Probably my least favourite Beefheart album.
It's his most accessible by a mile. Then go for Safe As Milk. Those two and TMR are the ones that i have and they're all great in very different ways.
Is the one I always recommend. Accesible but with *some* of the TMR weirdness. TMR is too much for a starting place & SaM is too straightforward compared to the rest, but both are classics.
It doesn't really sound like any of his other stuff at all. I would recommend 'Lick My Decals Off, Baby' for the same reasons that Poprivet recommended Shiny Beast. Lick My Decals Off is slightly superior, IMO (it's my personal fav), although both would work very well indeed.
I started with Trout Mask Replica and enjoyed it, but I can see how others might not.
something that I've always attributed to listening to electronica/IDM stuff. Probably wrongly. I think it also helps being a bassist - I'm always listening to what's going on under the surface. Whereas my sister once described Endtroducing's Stem/Long Stem as "a cacophony".
It's like the lean mean Trout Mask with one guitar. It's accessible compared to Trout Mask but it's still a bit weird for a first listen. And it owns Shiny Beast. I would maybe start with Clear Spot.
you could start with Doc at the Radar Station
Outside of the usuals I'd go for Strictly Personal, Mirror Man and the Legendary A&M Sessions.
(but Trout Mask and Safe As Milk are the ones to say really)
((Safe As Milk is my personal favourite))
(((Lick My Decals Off Baby is equally great but very different)))
((((check Willie The Pimp on Frank Zappas 'Hot Rats' album too))))