This depends on the scar. You want to make sure your scar has healed fully before you attempt a tattoo, and that means waiting at least a year. The scar (or stretch mark) should no longer be pink. Attempting a tattoo too soon would be painful and the ink may not hold very well.
Some people say the scar area is painless during the tattooing, but others say it hurts worse than unscarred skin. Keloids (raised ropy scars) are often quite painful, and some artists won't tattoo them. Raised scars in general will pose more problems for the artists, as they may not retain the ink well and may be very painful.
If you want to have a scar tattooed over, try to find someone who has experience in that type of tattoo. Scar tissue poses particular problems, and you want someone who knows what he or she is doing.