The Madonna Project: #4. “Who’s That Girl?” (1987)


For those who are new around here, you may wonder how The Madonna Project is already up to its fourth entry. To provide some background, I found myself entering 2019 wanting to write more about music on Optigrab. I came to the conclusion that the most interesting approach was to breakdown the albums of eccentric artists while tracking how their style grew over time. I started with Tom Waits, and boy was that ever a journey that hit plenty of highs and lows. In some ways, it made me wonder if I should even run a column like that again given that Waits had exhausted the subjects of loneliness, alcoholism, petty theft, and trains. Was it worth getting that personal with another artist? 

I eventually landed on Madonna because it sounded like a fascinating challenge. We all know the singles, but I hadn’t heard an album outside of “The Immaculate Collection.” Suddenly I became intrigued by the B-Sides, wanting to discover what made her albums so magnificent. The first three entries were published on Optigrab prior to its demise and were presented more as a song-by-song analysis. Things will be a bit different here, as I intend to write more of an essay exploring her albums on a cultural and even personal level. 


Which is why it’s a bummer that we have to start with “Who’s That Girl” (1987), her fourth “album” from Sire and Warner Bros. Records that is really a Madonna album in name only, 

While imperfect, her first three records had established an artist that was ready to provoke. Her performance of “Like a Virgin” on The MTV Video Music Awards had already made people gird their loins with pseudo-religious/erotic imagery. “True Blue” had taken her a step further as she matured with her best album so far. The craft saw her adding Latin rhythms, her lyrics were allowed to explore subjects like unwanted pregnancies in “Papa Don’t Preach.” As far as coming out parties went, that album managed to eviscerate any doubt that Madonna was going to phone it in. She was going to make her music more that was more confrontational, forcing the public to question the very idea of what a female artist could say. Many were excited to see what she would do next, and…

It was to star in a little movie called Slammer.

In some respects, it made sense. In 1985 she had gained certain acclaim for her role in Desperately Seeking Susan. However, her follow-up Shanghai Surprise opposite then-husband Sean Penn was considered a failure. Madonna personally believed that she wasn’t playing a character she could relate to. Shanghai Surprise was enough of a failure that Madonna had to convince the studio to let her make Slammer. She personally felt like she related to the bad girl with a good heart in protagonist Nikki Finn and wanted to go sillier. She would eventually hire James Foley as director. Having worked with him on the music videos for “Live to Tell” and “Papa Don’t Preach,” they were good friends. Foley was also the best man for Penn at their wedding, so there were already personal connections.

For those who wonder why we’re talking this long about Slammer when it doesn’t exist, you can blame Madonna. The film was shot in New York but took some time off in December 1986 due to snowfall. She decided to turn her attention to making the soundtrack, feeling the need to make one up-tempo and down-tempo song. It was during this time that she returned to the Latin rhythm for “Who’s That Girl?” Many compared it to her previous hit “La Isla Bonita,” but that would be deceptive given that it feels like the flavor was added later to make the song somewhat more enjoyable. She liked it enough that she forced the studio to change Slammer to Who’s That Girl? and thus the perfect symbolism for this whole endeavor began to take shape.

The film was often delayed because a certain
 co-star kept disappearing. Care to guess who?

Everything about Who’s That Girl? from album to movie felt like one compromise after another. Despite only doing four of the nine tracks, the record company considered a Madonna album despite her not appearing on the tracks by Scritti Politti, Duncan Faure, Club Nouveau, Coati Mundi, and Michael Davidson. In fact, there’s very little focus on any of these tracks within the film. Every key moment that involves music finds Nikki singing a Madonna song. It’s fine. She was coming off of three international best-selling albums. Any tassels that hung off of this film were favors she asked the studio to do. 


While the musician Madonna had matured, nobody could guess it from watching this film. Nikki is being released from prison after a wrongfully accused four-year stint. While she claims to have based her role on screwball icons like Judy Holliday, it’s easier to see her wanting to imitate James Cagney’s gangster mentality. Before she exits her cell, she adoringly strokes posters of Elvis Presley in Jailhouse Rock and Marlon Brando in The Wild Ones. Foley is clearly giving us a sense of the madness she will perform once she gets out. Whereas Madonna’s comments would suggest that she played her because she related to Nikki’s good heart, it’s hard to understand when Nikki illogically punches a cop while moments into her freedom and in a jailhouse facility. Within minutes she is behind the wheel, ignoring the geographic planes by which we all drive. She demands to go to the mall and shoplift a record store. As she’s leaving the mall, she drives onto an active train track and drives alongside a train before cutting it off. 

She is a cartoon character. This is made more apparent by the fact that she is giving us a helium-induced Brooklyn accent, managing to sound the right level of tough and girly. She at times has the hairdo of Little Orphan Annie but never is she sympathetic. The best that can be said is that Madonna’s commitment makes the role slightly, and only slightly, tolerable. She laughs at madness and you’re left wondering why she wasn’t put directly back in jail. This may be a story about getting revenge on the man she took the fall for, but she’s so guilty that the reckless endangerment she bestows over 92 minutes makes the idea of ending with police sirens booking her the only logical ending. But alas this is the late-80s and it’s a romantic comedy where bridesmaids are kidnapped and in a state of panic fall in love with men who clearly only want one thing. Let's just say it's not directions.

The only real public remarks we have of Madonna about this movie is from Foley. Following the film opening 10th at the box office, she told Foley “So it’s a flop, right?” The film failed and continued the belief that Madonna couldn’t act. However, her music career was still going strong. The soundtrack sold six million copies despite underwhelming reviews. The song “Who’s That Girl?” became her sixth number one hit, making her the first female solo artist to achieve this record. 


Even then, the four songs are among her least memorable. The other singles, “The Look of Love” and “Causing a Commotion” could work as B-Sides, but even then they weren’t particularly memorable. The former was an homage to Martha and the Vandellas, though anyone who had heard the “True Blue” album will be aware of how much more interesting she could take the 50’s pastiche. Even her being inspired by James Stewart’s performance in Rear Window reminded people of her James Cagney-laced “White Heat.” Like most everything else in Who’s That Girl? lore, it was a carbon copy of something that Madonna did better years before.

If there were any interesting notes about the soundtrack, it was “Causing a Commotion.” The song chugged along over the opening credits with Nikki Finn designed like a Betty Boop-esque woman walking down dangerous streets. The segment summarizes the set-up over three minutes and makes the film seem more like the madcap comedy it tries to be, but largely fails with a lackluster script. However, the origins of the song are much darker than one would expect for a song that would dominate the club charts.

It was well known that Madonna’s marriage to Sean Penn had been rather abusive. Their relationship was about to fall apart. In a Rolling Stone article in 1987, she said about Penn:
"I don't like violence. I never condone hitting anyone, and I never thought that any violence should have taken place. But on the other hand, I understood Sean's anger and believe me, I have wanted to hit them [the paparazzi] many times. I never would, you know, because I realize that it would just make things worse."
She described this act as “causing a commotion” inside of her. Suddenly the opening track to a screwball comedy where nothing mattered felt kind of depressing. While it helped Madonna cope with her own tragedy, it does create a powerful dissonance as to whether you dance or cringe whenever the song comes on. With all of this said, her music did get some glory with a Golden Globe nomination for Best Song in a Motion Picture for “Who’s That Girl?” Then again, another song (“El Coco Loco”) received a Worst Original Song nomination from The Golden Raspberry Awards. It was one of five nominations with Madonna winning for Worst Actress. 


One of the more controversial arguments was that the movie failed because of the Who’s That Girl? tour’s overlap. Much like the name shift of Slammer, the tour didn’t start off with that name. This was her second tour and the first international one. She exercised rigorously to get in shape, believing that everything had to be bigger and better. This meant increasing the number of screens that were projected from the stage. It is said that at one point Madonna turned to the screen and saw a picture of herself from years back, asking “Who’s that girl?” She had changed so much in just a few years…

And thus The Who’s That Girl? World Tour was born. 

Much like the film, it felt like things had been shoehorned in. This was supposed to be a moment to celebrate the achievement of the album “True Blue.” However, it was also seen as a chance to promote the soundtrack. Where the film had failed, Madonna was profiting off of it beautifully. It was the second top female concert tour of 1987 behind Tina Turner’s Break Every Rule Tour, earning $25 million and attendance of 1.5 million fans. Compared to the $7.3 million box office gross on the film’s $20 million budget, that made this another blip on Madonna’s radar. It wouldn’t stop her from acting or producing critically acclaimed best-selling albums. 

There may be fifty shades, but there's only one
degree separating this from Who's That Girl?

As for her buddy James Foley? He’ll be fine. He recently completed work on the film adaptation of E.L. James’ Fifty Shades Darker (2017) and Fifty Shades Freed (2018).

It’s weird to start this website on the fourth entry of an ongoing series, there’s also very little here that’s sensible about its place in Madonna’s history. While it leads to some of her most successful moments, it also found her few weaknesses. She was a pop star phenomenon, proving that she could sell six million copies of a record she barely appeared on. However, that doesn’t mean that the record is all that acclaimed or has any long-lasting appeal. It’s there for completionists only. Anyone else would be watching a forgettable screwball comedy that showed the limits of a radiating star’s appeal.

However, that star wasn’t going to be falling anytime soon. In fact, it was about to reach new heights. Having already played with sexuality and religion on “Like a Virgin,” she was about to enter a new ambitious era of her career. She allowed herself to open herself up to her audience with “True Blue,” but it was nothing compared to the sensation that she would end the 1980s on. “Like a Prayer” wasn’t just another record for Madonna. It was her grand statement.

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