Answer: These little pop-up messages are called Tooltips. There are a few things that can cause the problem you're asking about where the Tooltip doesn't show up, or doesn't appear to show up.
1. It can be an incompatibility with your anti-virus software, such as Norton. I'm not an expert on PC technical problems, but I suspect it sees the tooltip as an unwanted pop-up window. I don't have this problem, but if I turn my pop-off blocker on in Internet Explorer, I get the same problem the first few times I move my mouse over the Clock. After the tooltip finally shows up the first time, I don't have the problem again.
2. There's a known Microsoft bug (see http://support.microsoft.com/kb/912650)
that causes tooltips to sometimes hide behind the Taskbar. Depending on how wide your Taskbar is, you might see the top of the tooltip or perhaps not, if it's completely hidden underneath. There's no Microsoft fix for this bug, but other companies offer some software
to fix it.
Tooltipfixer
Tool Tip Manager
The Elder Greek on Windows XP mentions a free shareware solution for this.
Please note I cannot vouch for the reliability or safety of any mentioned software, nor can I know the compatibility with your PC. Always use caution when installing third party software.
If you just want to be able to see the date and time all the time, widen your Taskbar to a double height by dragging it upward. The time, day and date should stay on display.