True Blue by Madonna
Released in September of 1986, this song had a lucky number. The #3. It was the third single from her third album. It reached #3 in the US and stayed there 3 weeks. Sadly that's four #3's. Would have been really cool if there was only three #3s but what are ya gonna do?
The song was written as a love song to her then husband, Sean Penn. By the time the video was filmed, they were in the middle of a divorce, so maybe not so True Blue? Its composed as a retro throw-back song in the doo-wop style. While the lyrics are a love song to Sean, the music is a love song to the girl groups of the 50's and 60's that Madonna grew up loving and imitating.
The video even looks like a 50's doo-wop tribute. She's in a 50's diner, singing in a 50's convertible with her 50's style backup singers. Of the three back up singers (there's that lucky number again) one is her choreographer/best friend and was in 4 other videos for Madonna. Another is an actress who has been on Entourage (I never saw it) and was once Pee Wee Herman's girlfriend (like that's not super weird). She's in the dark blue shirt and was also in 4 other Madonna videos and was originally hired to do Madonna's hair and makeup on Madonna's very first video, Everybody. The third girl....No idea who she is.
Madonna changed her look for this video (surprise!!) and she had recently started working out and getting much more fit. I'm guessing her impending divorce had something to do with that. In any event, She always looked great to me, but this is an especially good look (I'm just sayin').