O ringing cylinders is quite common on supercharged or high compression drag racing engines. Which you do, the block or the head depends a bit on material of each and convenience. The usual choice is to do whichever is iron. On most engines it is easier to do the block since a lot of heads do not have round combustion chambers to index off of. It's not a do it yourself project as the groove has to be cut with high precision both in depth and width to match the wire that will be used. The wire will also need to be cut very carefully to length to make the exact size ring needed, but this is something that can be done by hand with great care. You will also need a head gasket that will work with the rings, usually made from copper sheet. If you want to persue this, you need to talk to a speed shop/engine builder/machine shop specializing in high HP drag racing engines.
Just for general interest: I made some pure platinum

O-rings for a custom built piece of equipment for a research project at NC state a couple years back!