20. Data In Drag From A Fistful Of Datas (1992)

Don't get us wrong: we love The Next Generation. If there's a gold standard for a Trek series to live up to - beyond the Classic series, of course - it's TNG. But much like the Classic series, TNG has several moments during its seven-year run that make many of even the most ardent fans embarrassed to be watching, especially if it's with a non-fan sort likely to say "What is up with this crap?" Unlike in other Trek series, the cringe in TNG follows a rough inverted bell curve: there's a lot of it in the first season, slightly less by the second, and progressively less until we hit fifth season, after which point the bad often seems to outweigh the good. So don't be surprised if this list seems weighted heavily towards the first two and last two seasons - TNG is not Voyager, which promises embarrassment from beginning to end. Unless, of course, the episode heavily features Data, in which case all bets are off and all cringes are on. The usual caveats apply: your mileage may vary, so what may make us cringe may make you laugh uncontrollably; our definition of a cringeworthy "moment" might entail a whole set of moments; and if you have suggestions about cringeworthy moments from other series to include in future articles, please tell us about them in the comments section below.There's so much that's cringeworthy about this episode, from the main idea to the execution, that it tends to scrape the bottom of the barrel on many fans' worst episode lists. The main cast seems to be having fun - especially Brent Spiner and Marina Sirtis, who gets to look somewhat badass for once in cowboy garb. But that doesn't necessarily mean the rest of us are. The whole mess reaches its nadir when the damsel in distress in the holodeck programme thanks Worf for saving the town - and it's Data in drag. Data. In drag. No amount of eyedrops, be they made of saline or hydrochloric acid, can wash that image out of your eyes once you've seen it. Guess it's a good thing the character in question wasn't working in a brothel, because the sight of Data in garters might've scarred us all for life.