I know Data tried to make Laforge laugh with his Mr. Tricorder parody in Star Trek: Generations Movie when he had this "emotion chip" ![enter image description here][1] Aside from this I only know the episode in TNG where Q loses his powers, being a simple human, and when returns to being omnipotent giving the Data the gift to laugh the very first time (as I recall). Was there an episode, where Data makes jokes intentionally and the crew is not laughing at him? Lore made some jokes, but he was bit cynical. [1]: https://i.sstatic.net/3NmR3.jpg