I know Data tried to make Laforge laugh with his Mr. Tricorder parody in Star Trek: Generations Movie when he had this "emotion chip"
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.