“The kid’s had too much reality lately, if you ask me”: Hollow Pursuits (TNG) vs. It’s Only a Paper Moon (DS9)

Barclay and Nog use the holodeck the way most of us would, if we could: they spend too much time in it.

“What could possibly go wrong?”: A Fistful of Datas (TNG) vs. Our Man Bashir (DS9)

Worf and Troi play Red Dead Redemption, while Bashir and Garak play Goldeneye.

“The dream dreams the dreamer”: Birthright, Part 1 (TNG) vs. Tinker Tenor Doctor Spy (VOY)

Data learns to dream, and the Doctor learns to daydream.

“It is you who are not real, sir”: The Big Goodbye (TNG) vs. Badda-Bing, Badda-Bang (DS9)

An early episode of The Next Generation starts a Trek tradition of holodeck malfunctions, while a late-series episode of Deep Space 9 lets the crew use the holodeck exactly as its designers probably intended: to pull holographic casino heists.