A good read about Windows Start Menu Horrors, as I'm writing this, I've a week old install of WinXp, and the menu already crossed to the second column, and that is with 1280x1024.
I usually arrange them in deep hirercies to fix this, but this means that I simply forget that I've stuff, and this is the whole point, isn't it?
The WinXp Most Used Programs in the start menu, however, is one of the best ideas for usability. I currently have it setup for 12 programs, and it's listing 80% of what I need to do during my work.
What other alternatives are there for this problem? Suggestions anyone? IIRC on Linux Gnome and KDE has the same metaphor, with deep menus. The Mac I'm not familiar with, did Apple solved this problem?