Madonna released the career-spanning compilation The Immaculate Collection in 1990, when she was at the absolute peak of her powers, and it’s one of the all-time greatest greatest-hits albums. The Immaculate Collection is just end-to-end bangers. It’s got seven #1 singles, and it also has a lot of truly iconic songs that had to be on there, even if they didn’t make it to #1: “Holiday,” “Borderline,” “Material Girl,” “Into The Groove.” Practically every song on The Immaculate Collection is a party-starter. To listen to The Immaculate Collection straight through is to marvel at a truly masterful pop career.

The Immaculate Collection is even more impressive when you think about what didn’t make it onto the album. Consider the Immaculate Collection omission “Who’s That Girl.” That’s the title song from the first movie where Madonna played the lead, and it was a genuinely big song. But Madonna didn’t make room for “Who’s That Girl” on The Immaculate Collection. She had too many great songs. A mediocre single couldn’t get a spot on The Immaculate Collection, even if that song was a #1 hit.

You couldn’t blame Madonna if she wanted to forget all about Who’s That Girl. Madonna made the 1987 movie when she was trying to turn her pop stardom into movie stardom, and things weren’t going too well. Madonna had played her first real dramatic role in the 1985 comedy Desperately Seeking Susan. The film was a critical and commercial hit, and Madonna was great in it. But Madonna had followed Susan by co-starring with her then-husband Sean Penn in 1986’s Shanghai Surprise, a catastrophic flop. After Shanghai Surprise, Hollywood still had faith in Madonna, and she got to make most of the important choices on Who’s That GirlWho’s That Girl is fully Madonna’s. It did even worse than Shanghai Surprise.

I’ve never seen Who’s That Girl, but it looks like pure doodoo. Madonna plays Nikki Finn, a screwball sexpot with a grating Betty Boop voice. At the beginning of the film, she’s framed for her boyfriend’s murder. After she’s been in jail for a few years, Griffin Dunne’s uptight lawyer guy, for reasons unclear from the Wikipedia plot summary, has to pick her up from jail just before marrying the daughter of the richest man in New York. Hijinks ensue, and Madonna and Griffin Dunne fall in love. Who’s That Girl bricked hard at the box office, earning less than half its production budget and getting intensely bad reviews.

It probably didn’t help that the movie seems very reminiscent of Jonathan Demme’s Something Wild, an actual masterpiece that came out just a year earlier. Also, Who’s That Girl came two years after Griffin Dunne had been a square yuppie dork on a wild adventure in Scorsese’s After Hours. So Who’s That Girl was a not-as-good version of a couple of things that had just been done very well. It smelled like a superstar’s indulgent vanity project because that’s what it was.

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