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I've hardly 100% anything but LEGO games.

In Ridge Racer Type 4 (PS1) I did collect all 321 cars and that's probably my biggest.
Or Angry Birds PC, with all the updates that had quite a lot to do.
Or Flatout: Head On (PSP), getting gold at everything was reasonable effort. But despite couple things, I don't feel that was nearly as tough as RRT4 or even Angry Birds.