10. Madonna - "Who's That Girl"
Fill your video with clips from the terrible film you’re promoting.
For reasons known only to Madonna, the venerable, mutable icon spends her video for “Who’s That Girl” wandering around a tacky set dressed as an androgynous 1920s waif and stiffly gazing at appropriately dire-looking clips of the film of the same name, her little-loved 1986 attempt to resurrect the screwball comedy. It doesn’t help that Madonna looks like a second-rate Cyndi Lauper impersonator in the film clips or that there’s a dispiriting sense of continuity between her terrible acting in the video and her terrible acting in the movie. If nothing else, “Who’s That Girl” performed a valuable public service by scaring people away from seeing the film, not that it needed much help in that department.



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