How to run wire through roof for lights?

I've never run wiring through my roof for lighting and am looking for ideas.

Power is coming from inside the cabin. I'm looking for common, clean, looking ways to drill and run it down through the roof. Water tight is the obvious goal.

Thanks for ideas/help

Drill bit, grommet, tiny bit of silicone.

I figured grommet type doo-dad and silicone. One's I've seen from the factory have a sleeved grommet to pass wire through body holes.

and as my brain starts thinking.. I now find sleeved grommets on Amazon.

Anyone like a particular type?

What are you using for lights using and how are you mounting them? My CB antenna is roof mounted but the coax penetration is covered by the base.