I’ve tried and tried and tried to figure this out, and just can’t.
How do I clear the list of documents that comes up under the “documents” tab off the Start button?
Hi RickJay
Right-click Start, and then click Properties. Or, if the Start menu is already displayed, right-click an empty area of the Start menu, and then click Properties.
Click Customize.
Click the Advanced tab.
Under Recent documents, click Clear List, click OK, and then click OK. Your most recently used documents are removed from the My Recent Documents folder. Note that this action does not delete the documents from your hard disk.
Blatantly ripped from Billy himself
Cause I’m a lazt typist. 
Do you mean ‘recent documents’?
If so, ‘navigate’ to Documents & Settings->login name->Recent
(where ‘login name’ is your login name)
delete all the files in that directory.
I think it’s possible to do it via the task bar properties also, but I am not at an XP machine so I’m not sure.
On XP, after you right click the bar on the bottom of your window. You’ll open the Taskbar and Start menu properties window. From there, click on Start Menu and then the Customize button. You’ll see a window named ‘Customize Classic Start Menu’ (or a variation, I use classic windows). There, you’ll see your clear button.
Man, I’m a slow typer! Um…What Daizy said! 
Me too.
You can also download an “unofficial” Microsoft toolkit (they developed it and make it available, but they neither guarantee nor officially support it) that will let you check a setting to have your recent-docs list cleared on every session restart (i.e. log off and log back on). It’s called TweakUI and is part of the PowerToys suite; here is the download page for XPPro.