The friend that got me into Macs recommended [link|http://www.lacie.com/us/products/product.htm?pid=10097|SilverKeeper] by LaCie. I tried it out first on my MacBook - was able to create a bootable backup of my MacBook's drive onto the new 500GB drive I'd picked up at Fry's.

Sadly it wasn't able to do the same for my iMac with the failing drive. 20K files were not able to be backed up, and it wasn't able to boot the resulting drive.

I plan to use this software going forward, once I finish reinstalling everything.