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My top five would have to be:
*DVD Decrypter (and SmartRipper--both do the same thing) *DVD Shrink (don't use it much anymore since i store stuff on an external drive now) *Handbrake *CCleaner (really does a good job, and it's free--beats the paid programs in many ways) *PDF Creator (although it does have some toolbars it installs, which I remove--that and MS Office now includes the capabilities of creating PDFs from the Office apps, but it's nice for printing pages from a browser to a PDF for example)
Those are about the top five freebies I use at least weekly, except for Shrink, which I use only rarely, but is still worth mentioning.
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