Star Trek – The Next Generation: 2×04 – The Outrageous Okona
This episode is just… it was hard to get through. So the Enterprise helps this Captain Okona, who is obviously meant to be a sort of puckish rogue straght out of an Errol Flynn movie. And sure enough, trouble soon find him and the crew of the Enterprise are caught in the middle of it. Captain Picard does some amusing restraint when trying to deal with the feuding, but that’s one of the very few highlights of this episode.
In addition, there’s another plot going on with Data trying to learn about comedy from a really unfunny comedian. There no safeguards on the holodeck to prevent jokes from dying. He’s also helped by Guinan, who I’m not sure I mentioned had joined the crew. She only appeared before in The Child IIRC, and is played by Whoopi Goldberg from off of that film, Jumpin’ Jack Flash. I think that’s the most famous thing she’s done other than this.
And yes, Teri Hatcher also appears in this episode operating the transporter, from off of Desperate Housewives and, who can forget, Lois & Clark: The New Adventures of Superman?