5. Data's Eulogy For Grandpa From The Schizoid Man (1989)
Why is it that so many attempts to make Data funny end up being a source of pain? In the case of Data's 'possession' by his 'Grandpa' in The Schizoid Man, it's not just Brent Spiner's oh-so-subtle acting as Data eulogizes himself (long story) that makes this one painful. It's the fact that the Enterprise crew honestly sees nothing wrong with this ridiculously over-the-top speech apart from the fact it's embarrassing, and it takes Picard a good two minutes to stop Data from finishing it. In the scene that follows this one, Picard doesn't do what any of us would do and ask, "Data, do you have a case of possession you're not telling me about?" Instead, he has a heart-to-fluid pump discussion with Data about why embarrassing himself and the audience is wrong, and it takes the perspicacity of Troi to convince him that something else is going on. God, second season episodes are awful, aren't they?