This does actually happen indeed. This is why NetApp storage solutions have an implementation of RAID 6. This is just in case you lose a second drive during the rebuild.
You can calculate the likelihood of a failure using the standard formulas listed on the following page link text As you scale to larger and larger numbers of data drives, the likelihood of just such a failure goes up. If you have enough disks you could push this number into the worry zone if you are using a RAID 5 with a huge number of data volumes.
I can tell you from personal experience that you certainly can have two drive failures in the same array within the same critical timeframe. Raid 6 saved me from having to restore from backup.
Hope this helps