Eurythmics ~ Who's That Girl?

from wiki: The music video became a heavily-played clip on MTV and further showcased Lennox's gender-bending image. In it, she appears as a nightclub singer performing the song (complete with 1960s-era blonde flip wig) and also as a male member of the audience. At the end of the video, the female Lennox is shown kissing the male Lennox.
Stewart appears in the video, escorted by a long series of different women, including a variety of guest stars, Cheryl Baker and Jay Aston of Bucks Fizz, Kiki Dee, Hazel O'Connor, Kate Garner of Haysi Fantayzee and all four members of Bananarama (including Stewart's future wife, Siobhan Fahey, and future group member Jacquie O'Sullivan, who would replace Fahey in Bananarama in 1988). The gender-bending pop star Marilyn also makes an appearance in the video at 1'35", apparently posing as another of Stewart's conquests (removing his glasses his trick appears to be noticed by Lennox but not Stewart). Despite the small role, Marilyn's appearance proved a high-profile move which helped lead to his own music career later the same year. Uncredited lookalikes for movie actresses Elizabeth Taylor, Sophia Loren and Meryl Streep also make an appearance.

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