For me it has to be Data and Joe Piscopo making spastic noises on the holodeck in the name of 'comedy' in "The Outrageous Okuna". Are there worse moments in Trek? Did anyone actually find that in any way entertaining?
Joe Piscopo trying to convince us he could teach comedy to Data was pretty bad. BAD with caps. Data could have taught him. "Rascals. "All of it. Even "Shades of Grey" is better than that. For the worst moment, I give you "Guinan" and Ro" bouncing" on Ro's bed. O. M. G. My eyes, my eyes! Although--all of NuTrek is close up for a tie. Just two hideous, predictable, clunky, unthinking non-Trek-spirit actioners from start to finish. Blech. For the worst moments, either the stupid, absolutely NOT exciting, boringly overlong, Matrix-like space dive to the Vengeance, or Carol Marcus stripping for blatant fanservice. Years ago I believed nothing would ever be worse than "Turnabout Intruder," but I was sooooooo wrong.
An episode where the central theme is about a dog urinating and then what happens to said dog and how its owner gets angry that others might get upset about it urinating. Moment:Me having to think about dogs urinating.
Spock joking about evil Kirk's assault on Rand in the closing moments of "The Enemy Within." Basically telling her "you know you liked it."
Data catching the disease in "The Naked Now"--actually the whole episode is pretty cringy. All comedy moments of The Doctor. The gazelle speech. STID.
I've long thought the TNG episode "Homeward" was the lowest of Trek. However, from reading these forums, I've learned that there are apparently a few other episodes scattered through the franchise--also dealing with grotesque interpretations of the Prime Directive--that may be even worse.
1994. The seventh season of TNG and the release of Star Trek: Generations. For awhile, I thought Star Trek would never be the same.
I used to think one of the lowest moments was Beverly having the big 'O' in Sub Rosa. Then I saw the brewery inside the Enterprise in Star Trek (2009).
Genesis when Barclay turned into the spider and every one turned into weird creatures. Voyager when Janeway and Paris turned into giant Lizards was totally lame. Enterprise These are the Voyages a crummy way to end a series. Spoiler: Enterpise spoilers I hated how Trip was killed off in the finale it's a really stupid way to kill offa Popular character totally unecessary The outrageous Okona wasn't funny with Data and Joe Piscopo in the holodeck I thought it was ridiculous not funny.
DS9 - episode "His way". The lowest moment was that Passionate Kiss on Promenade. Rene Auberjonois somewhat overacted his part. This kiss was too theatrical. On the whole, entire episode was doubtful if not the worst for Odo&Kira love story.
Dear Doctor - obvious reasons The Neutral Zone - actually, any time Picard gets all pissy about "no money" and treats the 20th-century survivors like dogshit Threshold - duh
Star Trek V: The Final Frontier. Period. There is nothing else in Trek -- even the worst episodes of VOY and ENT included -- that has proven so bad in the long term that it's impossible to watch it all the way through. (Merely underwhelming episodes like "The Outrageous Okona" or "Genesis" or moments of sexism in TOS don't qualify for me; they're irritants and nothing more.) But TFF has stood that test of time. Oh, to answer the OP's question: "The Outrageous Okona" was a bit dull, but nothing worse than that. Its main crime was that it was a waste of the charisma and presence of Billy Campbell (thanks Gary for the correction), who incidentally almost got the role of Riker.
Angel one & Code of Honor are lousy episodes.TNG season 1 had a lot of clunkers when it came to it's first season episodes.
I'd say any episode that was kid-centric, going all the way back to Miri & And the Children Shall Lead. I'm more forgiving of TOS, than I am of other series. There is no excuse for the row your boat scene in TFF. For TNG, the most cringe worthy episodes were, Sub Rosa, Code Of Honor, Icarus Factor, Justice, Up the Long Ladder,Masks, and except Half a Life...every episode with Lwaxana Troi The Thaw, Parallax, Tsunkatse, Thresh hold, Drive, Killing Game,& Spirit Folk episodes from Voyager were all Bad. For DS9, it's gotta be Valliant, any Mirror Universe episode
They were doing Jerry Lewis shtick. Apparently they wanted Jerry as The Comic, but there were schedule conflicts so they got Joe instead. So naturally, if you can't get the guy you want, steal his act. Low points for me were VOY: Fair Haven and VOY: Spirit Folk, for perpetuating Irish stereotypes. I don't know how they ever thought that was a good idea.