No matter how many times you wipe a drive, there are methods which bypass the drive's own read/write heads. For example, on a hard drive, the data is written in tracks, circular bands of magnetic patterns representing 0's and 1s. Due to thermal expansion/contraction and tiny errors in head positioning, you can erase or overwrite the information on a track effectively enough so that the drive's own heads cannot read it any more. However, the erasure is less effective towards the edges of the track, so that a tiny band on either side of the erased track contains a 'ghost' of the erased data. You can take the drive apart in a clean room and mount the platters in a special rig with micro-adjustable read heads and over a period of time you can recover the data.
Another method involves sawing the platters apart and mounting them one at a time in a special electron microscope and scanning the magnetic material, in effect taking a photograph of the magnetic patterns. By using one or more such methods an apparently erased disk can be made to give up its secrets. It might take weeks, but it can be done.
The only sure way to delete the data is to remove the platters (which are made of a special glass) and smash them and then melt the pieces in a crucible. The CIA requires this to be done and witnessed for the most sensitive data drives it uses.
Sometimes in a court case, the very fact that a disk drive has been professionally erased can be evidence.
The level of erasure which might be appropriate depends whether we are talking about identity theft, commercial espionage, international espionage, hiding legal porn from Mom or Wifey, or hiding illegal porn or terrorist material from law enforcement or national security agencies.