If ClipMate installs ok but crashes when you first run it (before you get to add any data, make any settings changes, etc.,) then it is probaly a video driver problem.
Try reducing the amount of hardware acceleration in the video properties of your desktop. Right-click on the desktop, Properties | Settings | Advanced. One of the tabs in there has this option. On XP, system it's under Display Properties | Settings | Advanced | Troubleshoot", but it could also be something like "Performance" on 2000. On Win98 it's under Settings | Advanced | Performance. In any case, there should be a slider for "hardware acceleration". Drop it down to the lowest level (as a test) and see if that does anything. If that helps, then increase the setting as much as you can, and still have ClipMate run ok.
One user reported that he had trouble with his NVidia Riva TNT, and the problem went away when he updated it with the "win9x-ME_23.11.exe" update file. Worked like a charm.