Hi Scotty,
I have 1990 Chevy Silverado 5.7L V8 4x4
Driving at night and the head lights turned off for few seconds and turned back on by itself. It kept doing it for a period of time ( long minutes) then it stayed on.
I didn't drive the truck at night since then.
Where should I start looking at this horrible problem? {black}:afraid:
Thank you Scotty
Yours has a circuit breaker built into the light switch
So is the issue with the 35 year old switch or is there a short to ground in the circuit.
You say it does it a few times and then the headlights stay ON.
If this were a short to ground they would keep tripping the breaker.
I'd replace the headlight switch and see if that solves the problem.

the head light switch is not the age of the truck, I've replaced it few years ago
Where should I start looking at this horrible problem?
the headlights would be a good place to start.
It's an electrical connection issue, so anything from the bulb itself, to the socket, wires, relays etc. all the way back to your fusebox can be loose , corroded, chafed etc.
one light or both?
grab yourself a schematic on charm.li and use it as a reference
both lights, the dash lights stay on while doing it
okay so problem likely exists before the circuit splits into right & left