In The Number Ones, I’m reviewing every single #1 single in the history of the Billboard Hot 100, starting with the chart’s beginning, in 1958, and working my way up into the present.
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 Girl. Who’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.
Madonna figured she needed to do a comedy, so she pushed hard for Who’s That Girl. She chose James Foley as her director; Foley had directed Madonna’s then-husband Sean Penn in At Close Range, and he’d also served as best man at the Madonna/Penn wedding and made Madonna’s videos for “Live To Tell” and “Papa Don’t Preach.” (Foley later admitted that taking the Who’s That Girl job was a mistake.) At first, Who’s That Girl was supposed to be called Slammer, but once Madonna came up with the song “Who’s That Girl,” she changed the title of the movie to fit the song.
When she was planning the movie, Madonna told her “Live To Tell”/”Open Your Heart” collaborator Patrick Leonard that she needed an uptempo song and a downtempo one for the soundtrack. Leonard wrote the music for “Who’s That Girl,” and Madonna wrote the lyrics and the title. Both of them shared production credit. The whole song was finished in about a day, and it sounds like a song that was finished in about a day.
Madonna had been flirting with Latin pop and style since she first showed up on the scene, but “Who’s That Girl” came out at the moment when she was really going all-in on that stuff, to the point of absolute shamelessness. A few months before she released the “Who’s That Girl” single, Madonna reached #4 with the True Blue jam “La Isla Bonita.” That song would be pure risible kitsch — clumsy fetishization of exoticized culture — if it didn’t fucking rule. For all its tone-deaf quasi-Latin accents, “La Isla Bonita” is one of the swooniest jams in a career full of swoony jams. That bridge? “I want to be where the sun warms the sky”? Fuck. (“La Isla Bonita” is a 9.)
“Who’s That Girl” is a distant echo of “La Isla Bonita.” Madonna is still on her fake-Spanish shit. The song’s hook is full-on Spanglish, and Madonna does not sound comfortable or fluid singing it, even if she wrote the lyrics herself. The song’s groove — the sparkly synths, the percolating congas, the soft ripples of guitar — are just Madonna and Patrick Leonard taking everything they’d just done on “La Isla Bonita” and hitting repeat. There’s juice in that formula. The “Who’s That Girl” beat is slick and strong, and there are some catchy melodic bits on the song. But the track just doesn’t work the same way.
Confidence has always been central to Madonna’s appeal; she had a swagger that few of her ’80s-pop peers could match. But “Who’s That Girl” might be too confident. Madonna sings the whole song in the third person, and it’s all about how you should be careful around this extremely hot girl because she’ll break your heart: “When you see her, say a prayer and kiss your heart goodbye/ She’s trouble in a word, get closer to the fire.” (Those lyrics are trash.) There are lots of pop songs about mythic jezebels, and some of them, like Kim Carnes’ “Bette Davis Eyes,” work because you can hear the admiration and envy in the voice of the person singing. But when Madonna is singing about herself, you don’t get that at all.
Technically, I suppose Madonna is really singing about Nikki Finn, her character in the movie Who’s That Girl. In Fred Bronson’s Billboard Book Of Number 1 Hits, Madonna says that the songs on the Who’s That Girl soundtrack “aren’t necessarily about Nikki, or written to be sung by someone like her, but there’s a spirit to this music that captures both what the film and the character are about, I think.” This is bullshit. “Who’s That Girl” is clearly supposed to be a song about the girl from Who’s That Girl. Since Madonna is the person playing that girl — and since she’s the driving force for the movie in the first place — “Who’s That Girl” sure feels like Madonna singing about herself. That means that Madonna is singing about herself, in perfect sixth-grade Spanish, as a “señorita más fina.” It’s pretty stupid!
“Who’s That Girl” should probably be remembered as a total fiasco: A pop star ripping off her own most recent single, indulging in some halfassed cultural appropriation, and spending the entire song singing dumbass lyrics about how más fina she is. The track should be the stuff of snarky mid-’00s VH1 countdowns. But Madonna was on such a roll in 1987 that nobody really got mad about “Who’s That Girl.” The song quietly cruised to #1, and then everyone agreed to forget that it had happened. And it’s not even that bad a song! It’s just a generic, competent example of the kind of dance-pop that was popping back then. On its own, “Who’s That Girl” is a perfectly OK piece of music. The song only really stands out in the context of Madonna’s historic run. It’s a rare uninspired moment.
Madonna only had four of the nine songs on the Who’s That Girl soundtrack, but the record was essentially marketed as a Madonna album. Her name and her picture were on the cover, and none of the other artists on the soundtrack (Scritti Politti, Club Nouveau, Madonna’s friend and Who’s That Girl castmate Coati Mundi) released their tracks as singles. The Who’s That Girl soundtrack is a pure quickie cash-in, and it still went platinum and yielded two big hits for Madonna. Madonna didn’t even bother to make a video for the sleek club jam “Causing A Commotion,” and it still peaked at #2. (It’s an 8.)
After the movie flopped, Madonna still salvaged the Who’s That Girl name. She spent the summer of 1987 on the Who’s That Girl Tour, which hit three continents and pulled in $25 million — roughly four times what the movie Who’s That Girl earned at the box office. Madonna just could not fail. Who’s That Girl had been a notorious bomb, but it shared a title with a #1 single and a successful tour, and it didn’t hurt its star in any real way. Soon enough, Madonna would once again reinvent herself, and she would continue surfing on the zeitgeist for another decade-plus. We will see her in this column many more times.
BONUS BEATS: Here’s the freaky DIY-synthpop “Who’s That Girl” cover that a band called the Bubonic Plague recorded for the 2007 indie rock Madonna tribute compilation Through The Wilderness: