20 Most Cringeworthy Star Trek: The Next Generation Moments

18. Joe Piscopo Teaching Data Humour From The Outrageous Okona (1989)

Data's attempts at humour are, ironically, often some of the least funny moments in the series. He's a machine, they keep telling us, and you can't teach a machine to be funny. Unless it's a sex toy. Wait, Data was once one of those, too. Anyway, in The Outrageous Okona, an episode that has a big load of cringe to begin with, Data decides it's time to get some instruction on being funny, so he goes to the holodeck. Actually, he goes to Guinan first, and it doesn't work because she gives him poor jokes like "You're a droid and I'm a noid." Jumping Jack Flash was a while ago, wasn't it, Whoopi? When Data goes to the holodeck, he pulls up a twentieth-century comedian named - wait for it - Ronald D. Moore. I'm sure the Battlestar Galactica showrunner must look back at that homage with pride even to this day. The comedian in question, played by former Saturday Night Live regular and inveterate bodybuilder Joe Piscopo, tries to teach Data to be funny... by doing Jerry Lewis impersonations. Hilarious if you're French, so Picard would've loved it, but for everybody else... ugh. The rumor about this episode is that the show's producers actually wanted Jerry Lewis to play the part of the Comic, and when he turned it down, they got Piscopo to do impressions of him. Whether the scenes with the Comic would've been funnier (or even funny) or not had Lewis participated is something we can only dream about. Or have nightmares about, take your pick. It's pretty nightmarish as it is.