(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.
I was fine with them. They weren’t my favorite episodes, but as @zero_spelled_with_an_ecks mentions, it offers a different facet of the character. The idea of the stern, “stuffy” Picard indulging in 1940s American noir roleplay is amusing to me. It’s one of those things that’d come up in one of those awful “two truths and a lie” icebreaker activities.
They led into Picard mowing down Borg with a Tommy gun in First Contact, so they’re a-okay with me!
Incidentally, I just watched The Big Hit, which came out in 1998, right around the time that In The Pale Moonlight aired, and it features Avery Brooks chewing scenery as a cartoonishly over-the-top mob boss, so I like to pretend that it’s a holosuite program he ran to loosen up after the events of the episode.
I hated them. I also hated the Chaotica/Captain Proton episodes on Voyager. I’m sure they were fun for the people involved, but I got second hand embarrassment trying to watch them.
I found his raspy, gravely voice unbearable. I can’t stand to hear him sing. I fast forward though it every time.
Ironically, I rather liked his acting and enjoyed his character otherwise— although I think the writers relied a bit too much on his character/the Vegas lounge program schtick, and “Mirror Vic” was an absurdity that should never have existed.
I had a hard time buying Jean-Luc Picard as a hard boiled PI, but I suppose that’s the point of a holodeck program- you get to fantasize about being something you aren’t if you want to.
Picard being a fan of the Dixon Hill novels, on the other hand… that seems out of character.
I know a guy who is a literature snob and is probably the last person I would have expected to really get into Raymond Chandler novels. Anyway, he was raving about those books so I read a few. It turns out that Chandler was a phenomenally weird wordsmith. Inventive, funny, and unexpected. If you're looking at midcentury American writers, Chandler is hugely underrated. Maybe in a few centuries he'll get his due.
Sure, it's detective pulp. But it's detective pulp that's been given a strong hallucinogen and whacked over the head a few times before waking up in the desert.
Eh, I have to admit, I have a hard time buying it, too. This is a guy who reads Shakespeare in his spare time, not trashy, pulp detective novels from the early-mid 20th century. He even thought taking a trip on The Orient Express would be too indulgent. Picard liking Dixon Hill novels makes no sense. Just like off-roading in an ATV.
I liked seeing the actors get to play some different roles and I liked seeing the fantasy life of the characters whenever there was something off the beaten path. It helps round everybody out, in the same way that playing an instrument or having a pet does.
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