Star Trek

(Response is more about holodeck centric episodes in general).

I liked how Data would go all in on the roles he played. And Picard's frustration at frequently getting called away from his fun time.

I didn't like the Moriarty takes over the Enterprise ones, you'd figure they'd sandbox the holodeck environment and specifically set it up to prevent situations like that. Maybe even make them incapable of seeing through the 4th wall in fantasy/entertainment programs (though I can see the usefulness of being able to do that for engineering exploration and might have just talked myself into not hating that as much because I had forgotten about the practical uses of the holodeck).

I've also always found the focus on holodeck scenarios relevant to the 20th and 21st centuries culture made it harder to suspend disbelief. I don't think our current entertainment is the peak that everyone would come back to all the time. Like you'd figure LaForge would have done the whole "help build and troubleshoot the first warp drive" on the holodeck before doing it for real in First Contact. Like I get why they focus on things we know rather than having to make up more lore, but they made up a lot of lore each time they visited a new planet.