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It it the Pet Shop Boys' "I'm With Stupid"? https://www.youtube.com/watch?v=q32JAfaEPbk
There were several Pet Shop Boys videos in the early 90s (from their album Very) that had them wearing orange shirts and striped cone hats. The video for "Can You Forgive Her?" has them rowing a boat too, though it's not black: https://www.youtube.com/watch?v=o5Q7ZE3jkPM

More like "music videos", I guess: You see, there's this eighties dance night I go to sometimes, where they have music videos projected on a screen behind the dance floor, but the videos are to completely different songs from what the DJ is playing. This one particularly stood out as being a Surreal Music Video - I mostly remember that it involved people wearing orange shirts with orange and white striped cones on their heads, who were riding on black gondolas. The videos usually are from the same time period the actual DJ set is, the eighties up to the early nineties, but it could even be something later than that; For instance, I've seen them throw in Fatboy Slim's "Weapon Of Choice" video once, presumably because Christopher Walken dancing around a hotel room and defying gravity is just that cool.
Edited by MikeK