Do you know Madonna videos???
I remember a video from Madonna and not the name of the song!! Please help! In the video I think she is a shop girl or working girl and having sex with strangers or a werid boyfriend. But watching her from a directors chair is a famous actor, (maybe Christopher Walken?) so he makes it seem as though they are shooting a video. But it's not...he's like an older, wired voyeur and she knows it....anyone remember anything like that? Thanks so much 
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Here's a link to the video for "Material Girl" by Madonna. From the description you gave, I'm thinking this might be what song you're talking about. If not, sorry. Have a great weekend!
http://www.youtube.com/watch?v=nmW2XwU5dB4
"Bad Girl"