The video to "Head Over Heels" was directed by Nigel Dick, who would later direct Britney Spears in "Baby One More Time
." Roland Orzabal gave Dick the concept, which was meeting a beautiful girl in the library and growing old with her. He also suggested many of the very random images, like the rabbi and the chimp. There's even an homage to the movie Ghostbusters
in a scene where Orzabal pulls a card catalog drawer and the cards go flying.
Ripe for parody, in 2008 a "literal" version appeared on YouTube which contains dubbed lyrics that poke fun at the video's visuals. See that here