I always felt like the Win98 icons were subpar because they didn't have a consistent perspective and the shading was unnecessary and not very well done. Everything is shaped like flat surfaces but shaded as if it's rounded and bulge-y.
The Mac System 7 icons were what made me fall in love with icon design. There are so crisp and legible, and create a consistent metaphor and perspective that spans the entire desktop and glues it together. And they still manage to have a little charm and warmth.