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I'd personally put US v. Miller on the list instead of DC v. Heller.

Wickard v. Filburn deserves a mention too.

Oh yeah, Wickard is ridiculous. If you grow wheat in your backyard to feed to your own pigs, that's interstate commerce.

I’ll raise you a Gonzales v Raich, wherein the cultivation of 6 marijuana plants in a backyard for personal use is interstate commerce.

Miller is an interesting one. Ruled that only weapons of war were protected, and now we're hearing "weapons of war have no place with the people"

Don't forget "machine guns aren't weapons of war" which is also quite a bit of a head scratcher!