Voyager Season 1
"Heroes and Demons"
I cast... GLOWY OCTOPUS!
Harry Kim decides to run a holodeck program for Beowulf, but he disappears. Tuvok and Chakotay go in after him, Chakotay shows off by knowing what century Beowulf was written off the top of his head, and then they also disappear. It's somehow related to a something something outside (plasma field? subspace anomaly? subspace plasma field anomaly?). Janeway decides to send the holographic doctor in to the holodeck on his first "away mission" to try and find out what the heck is going on. He gets his first kiss, loses an arm, gets the arm back, and the girl dies. It turns out that Grendel is actually an alien entity and it all works out at the end, but none of that is as important as the crazy hairstyle Janeway is sporting in this episode:
Who green-lighted this!? WHO?
Voyager, Season 2
Where there's a holodeck episode, Barclay can't be far away.
After some unexplained events, the Doctor starts suspecting that he's a real person and the rest of the crew is holographic. Barclay shows up and verifies this, saying that the Doctor is actually Doctor Zimmerman (the holoprogrammer who created the EMH) and he has been running a holodeck simulation for a few weeks of how the long-term deep-space isolation would affect a mixed crew of Starfleet and Maquis crewmembers in the Delta Quadrant. Barclay does not explain why anyone would feel the need to run such a simulation, or why they would choose to play the role of the holographic doctor that can't leave sickbay, but that's not the weirdest thing about this episode. Barclay tells the Doctor to destroy Voyager so the program will end, but the Doctor has a nervous breakdown about whether he's a real person or a hologram. Turns out the Doctor was in the holodeck on Voyager when some radiation something something made him go completely insane. When it all ends, he's a little bit "yay, I'm a hologram and things are right in the world!" and a little bit "well, fuck, I guess Kes isn't my wife after all."
It just ain't a Voyager holodeck episode if the Doctor doesn't get his smooch on.
This is one of my favorite Voyager episodes, and it's completely silly. A spatial anomaly is smooshing the ship, changing the configuration around, and the crew (those we care about, anyway) keep ending up back in a holodeck simulation of Sandrine's bar and pool hall, because it's in the dead-center of the ship and is the last area to get squished. They all run around like dorks for 43 minutes, squabbling with each other and the none-the-wiser holograms as they try to save the ship, and in the end everything is fine because the spatial anomaly was actually a life form "saying hello." Dear spatial anomaly life form: do they not have personal space in your dimension?
Voyager Season 3
Working episode title: Single White Hologram.
Harry Kim, Pathetic Ensign of the Stars, falls in love with a hydrosailing teacher in a holographic beach resort. He overreacts to Tuvok by claiming to want to purge all emotion. Tuvok, Long-Suffering Vulcan, decides he has nothing better to do and goes along to meet the holographic babe, Marayna, in order to teach Harry detachment. Only one problem - Marayna turns out to be smarter than the average hologram, and also a bit of a psycho stalker. Tuvok is intrigued by how different she is by ordinary holograms, but not intrigued enough to be okay with her stealing the doctor's mobile emitter, taking control of the ship and threatening death and destruction if he doesn't stay with her on the holodeck. Turns out Marayna is actually a reclusive alien scientist who coopted the holographic character for fun and then ended up obsessing over Tuvok. The Doctor showed up in this episode long enough to get his requisite kiss:
Haters gonna hate.
Leave it to Beaver: The Next Generation.
The Doctor creates a holographic family for himself to come home to at the end of the day, which is kind of fabulous. Because he's generally clueless and apparently got his source material from somewhere in the 1950s, he builds himself a submissive housewife and brilliant, reverent children. He invites Kes and B'Elanna over for dinner, who are respectively bemused and dramatically offended by the perfection. B'Elanna, who has probably the most dysfunctional family life of anyone on board, offers to make the program more "real". The wife no longer likes him, the teenage son parties and plots violent acts with Klingon friends, and daughter Belle does dangerous sports and throws tantrums. Rather than yell at B'Elanna, the Doctor decides to make it work and falls in love with his difficult kids, just in time for Belle to get fatally injured and DIE. It makes me angry that the Doctor or B'Elanna don't just fix the program to make her survive - he's pretending they aren't holograms, but they are, and he has the capacity to save her, so JUST DO IT BECAUSE IT MAKES ME CRY EVERY TIME, DAMN YOU. Anyway, B'Elanna killed the Doctor's kid. ALSO:
B'Elanna's interest in romance novels: CANON.
We're not even done with season 3, folks. Pull up a chair.