TNG, Season 3:
"Great. Another woman who won't get personal with me on the holodeck."
The episode opens with Geordi winning the Trying Too Hard award when he brings a date to the holodeck and scares her off with a violin serenade. Later, to save the ship, he recreates the Utopia Planitia drafting room where the Enterprise was designed and a holographic version of Sexy Ship Architect Dr. Leah Brahms, who offers to make him Italian food and they kiss and really, I'm surprised anyone on this ship ever gets any work done. Most shocking: there isn't a single holographic malfunction! The episode seems to be about the value of computers vs. humans, because the big issue is whether to let the ship's computer pilot the ship out of danger without human help, or have the humans do it without the computer's help. They pick the humans, and save the day, but Geordi still falls in love with the ship's computer, so the moral isn't clear.
"A Matter of Perspective"
Riker protests holographic!Riker's amorous advances (toward the alien chick).
I don't even know why I included this in my marathon. The whole episode takes place on the holodeck, with everyone's testimony in an extradition hearing being rendered holographically, because that's how justice happens in the future, or something. Absurdly, the holographic recreation of the science station generates real krieger waves that are disrupting the ship's systems. Whatever. Next!
Program warnings: RPF, AU, midgets.
This episode is amazing. Painfully shy Lieutenant "Broccoli" Barclay recreates the ship's crew on the holodeck so he can play-act at being a suave, manly sex god. In the real world, everybody hates him, because he's totally weird and never shows up to work on time because he's busy being a suave, manly holodeck sex god. Hilarity, awkwardness, and some bizarre consent questions ensue. Should it be legal to recreate crewmembers on the holodeck? What if you just want to have a fencing match with a midget Riker? Why the hell did I spend my whole childhood thinking the random guy who played Lt. Duffy was Matthew Broderick?
Not Matthew Broderick.
TNG Season 4:
Riker "ends this charade!"
Riker is trapped in the Inception of alien holodecks. First, he believes that he's in his own future and has lost his memory. In the future, he has a son, the Federation has a new treaty with the Romulans, and Deanna has the most ridiculous stripe of gray hair. The son's mother is apparently Minuet, Miss Holographic Sultry Jazz from "11001001," so Riker realizes that it's all a sham. Then it seems he's being held captive by superbly inept Romulans. Then he learns that he's actually being held by an alien child - Riker's "son" - who has been living alone on the planet with only a holodeck for company. It's actually really awwwww! when Riker invites the kid to the Enterprise, where we never see him again.
TNG Season 5: Nothing! Y NO LOVE SEASON 5!?!?
TNG Season 6:
"A Fistful of Datas"
Data, Troi and Worf in cowboy hats render your argument invalid.
I've heard a lot of people hate this episode, and I don't get it! It's so much fun! Data and the main computer cross some wires, and things go a little batty. Worf (grudgingly) and Deanna (ecstatically) are partaking in an "Ancient West" holodeck adventure co-written by Alexander and Lt. Barclay of I am the Goddess of Empathy, cast off your inhibitions fame, when the computer glitches start messing with the program. The safeties go off-line (of course), the holodeck is sealed off from the rest of the ship (naturally) and all the program's characters are turning into Data. One of the evil Datas kidnaps Alexander, and 'Counselor Durango' decides that they should play out the program so that it will shut itself off. They all survive, and Worf learns the true meaning of Christmas. Outside the holodeck, Data starts talking like a cowboy gunslinger, and the Beverly Crusher Drama Club's rehearsal derails when Riker's script turns into Data's poetry. (I don't know why, but Riker doing a dramatic reading of Data's poetry is one of my favorite scenes from all of TNG.)
Holodeck safeties are a TERRIBLE IDEA! "This program can kill you!" should not be a setting that can be switched on and off. Why not just write the programs so that weapons and characters are non-lethal? This seems like it would solve a lot of damn problems!
"Ship in a Bottle"
Secret hologram Doctor Crusher examines surprise human Doctor Moriarty for unwitting Picard.
This episode is pretty much the ultimate holodeck episode, in that no other ones really needed to be made after this (but we keep making them, because they are lolarious). The Nefarious Doctor Moriarty from Season 2 is accidentally reactivated, and he walks right off the holodeck exclaiming "I think, therefore I am!" It appears that he has spontaneously become human, and he begs a thoroughly baffled Picard to find a way of turning his holographic lover real as well. It turns out that Moriarty has recreated the Enterprise - and all her crew, right down to Crusher worrying about morality - on the holodeck itself, so Picard, Data and Barclay won't realize that they're still inside. Picard gives the holographic Enterprise his voice-command codes, which Moriarty than uses to commandeer the real Enterprise, all from within the holodeck. His goal is to free himself of the holodeck and become real. Once they figure out they're on the holodeck, Picard uses the holographic holodeck within the holographic Enterprise to program yet another Enterprise to trick Moriarty into a flash drive. It's like nesting dolls of craziness. At the end, Picard offhandedly suggests that maybe their whole universe is actually someone's computer program somewhere, and Barclay never sleeps again in his life.
In short, this episode is freaking brilliant. The exposition in the teaser is horrible, but skip that and it's one of the best things ever. I have seen this episode before and I still fall for parts of it. A-MA-ZING. Sadly, this means this marathon might be all downhill from here.
(Next up might be "Emergence"? I have seriously never been able to figure out what is going on in that episode. Maybe this time! Stay tuned!)