In terms of getting your money's worth, added content etc... Not so much having to do with how good the base game itself is.
Off of the top of my head, I'm thinking something like Beyond the Dark Portal for WC2 or Broodwar for SC. I think because essentially you're getting an entire new game that is (I think) larger, more difficult, and includes more units than the original.
I'm also enjoying Opposing Force for HL and Blue Shift for the first time, and I think they deliver.
My honorable mention would be Lord of Destruction for D2.