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You mean on the tailgate? That is a good question. That was a question here many many years ago. I don't think we got a definitive answer then. Maybe someone knows now.
I've seen people lay a sharpie on it's side and go around the letter at the edge to give a paint line. Then come back with brush and fill in. Gives a pretty straight edge. I have done it on license plates
Concur with the hard rubber roller. This is the sort of roller that would be used to apply ink to a sheet of type set in a printing press or to a wood cut to make a print.
I use a paint pen that I pick up at my local ACE HARDWARE. It has an internal stirring ball, and a felt tip that you depress to release more paint. This is obviously not how it was done in 54.
TO paint the FORD letters on my 70 F-350 flatbed I took a foam brush and cut it to the width of the letters and used that to apply the paint. It looked OK. It might be harder with a cursive script but I think that is easier then taping it off. When I got my 54 painted 17 years ago the body guy painted the letters, then taped them off then painted teh tail gate.