Bad Movie Night: The Dopey, Kitschy Appeal of Madonna’s ‘Who’s That Girl’

Madge's 1987 screwball comedy is a mess, but it's hard to ding a movie that works so hard for your affection.

Welcome to “Bad Movie Night,” a biweekly feature in which we sift through the remains of bad movies of all stripes: the obscure and hilarious, the bloated and beautiful, the popular and painful. This week, to commemorate the 30th anniversary of its release, we look at the screwball Madonna vehicle Who’s That Girl.

Surmising the motivations and chain of decisions that result in the making of a bad movie is a tricky bit of business, but it’s not that hard to put together some educated guesses about how Who’s That Girl came into the world. Madonna’s previous big-screen effort, Shanghai Surprise, was a very loud critical and commercial failure, and the primary slam was that it took itself too damn seriously. So the singer/actress went back to what worked, and her hit 1985 debut feature, Desperately Seeking Susan, was a New York-set comedy. So she needed another one, stat.

Who’s That Girl is a blatant mash-up of Bringing Up Baby (bespectacled intellectual, dizzy dame, jungle cat), Scorsese’s After Hours (with Griffin Dunne reprising the role of a button-up type who spends one long night being chased through NYC), and the previous year’s Something Wild (in which a sexy free spirit meets uptight yuppie), but PG-13. It often plays with that kind of formulaic calculation; the opening “pitch meetings” sequence of The Player didn’t come from nowhere. The producers are ‘80s super-powers Jon Peters and Peter Guber, two years away from Batman; the cinematographer is Jan DeBont (who would go on to direct Speed and Twister, among others). And the director is James Foley, whose weird career brought us both the highlights of Glengarry Glen Ross and Reckless, and the low-lights of Perfect Stranger and Fifty Shades Darker. (His previous film was At Close Range, featuring an original Madonna song and a lead performance by then-Madonna husband Sean Penn, which is presumably how he got the gig.)

The film begins with an animated Madonna emerging from the Warner Brothers logo, a Looney Tunes connotation that, mixed with the animated credits and the opening song “Causing a Commotion,” establishes the tone they’re going for (if not the one they always achieve). Madonna is Nikki Finn, a recently paroled con; Dunne is Loudon Trott, a tax attorney, a fact established by his first line, “I’m not an animal trainer, I’m a tax attorney.” He’s also an prototypical yuppie, a piece of information most firmly established when he later notes, of the Rolls-Royce he’s driving for the day, “I’m more a Volvo man myself.”

Loudon is about to marry blue-blood Wendy Worthington (Haviland Morris); he works for her father, and as she notes, “Daddy has big plans for Loudon.” But “Daddy” (the great character actor John McMartin) has a small plan first; he nees Loudon to rearrange his many errands on this, the day before his wedding, to pick up Nikki from prison and put her on her bus to Philadelphia. He doesn’t explain why he’s taken such a keen interest in this ex-con, but it sounds simple. “Drive her to the bus station, mile and a half, it’ll take five minutes,” he assures his future son-in-law, though if that were the case, it wouldn’t be much of a movie. That’s not the case; it turns out, she wants to clear her name, and needs Loudon to help her get to a safety deposit box with the information to do so. Hijinks ensue.

In other words, it’s classic one-long-day/night-in-NYC movie, full of zany characters, car chases galore (up to and including one, yes, down a sidewalk, knocking over vendors), plenty of gunfire, our heroes leaping from rooftop to rooftop, and a vaguely racist trip to Harlem. The script isn’t terribly clever (writers Andrew Smith and Ken Finkelman think the height of wit is a scene in which our uptown/downtown protagonists are mixing up the definitions of “fencing”), frequently harboring the delusion that complications, in and of themselves, are funny – not the reactions of well-established characters to them, or smart dialogue bouncing off them. So we don’t just have the safety deposit box McGuffin or the impending nuptials to deal with; there’s the delivery of an endangered jungle cat to a rich client, and the kidnapping of the bridesmaids, and angry gangsters in pursuit, and a pair of typical ‘80s-movie mismatched cops keeping tabs, all to further busy up the plot.

And, of course, it’s an opposites-attract romance, in which our Loudon initially loathes this low-class troublemaker, but finds himself drawn to her sense of danger and casual sensuality. Sure, he spends the first half barking things like “Listen to me, you little insane person,” but by the hour mark, we’ve got a montage of Loudon walking and daydreaming about Nikki, to the sounds of (what else) a Madonna song with painfully on-the-nose lyrics. And that’s followed by the inevitable slow-tilt close-up of our gal Madonna, revealing how nicely she cleans and glams up; she makes bedroom eyes, chews on her bottom lip, and purrs “Louden, it’s been a long time.” (Side note: Who’s That Girl shares with Nothing in Common the weird, apparently specific to the mid-‘80s notion that animal breeding is a giant turn on for observing humans.) It’s easy to see why Madonna took Who’s That Girl: it’s a movie that presents her, through action, photography, and explicit references in dialogue, as tough, funny, street-smart, and sexually irresistible.

However, since Loudon’s engagement is part of the plot, the script has to give him an escape valve – so, as a running gag, he keeps encountering cab drivers who say of Wendy, “I had her in my cab once.” You see, if the fiancé turns out to be promiscuous, then we’re all okay with him hooking up with Madonna (gotta say, all things considered, it’s sort of odd for her to appear in a slut-shaming flick). At any rate, they spend the night together and then part ways, leading to what’s basically an Arthur ending, wackily but weakly gathering all the strands for the aborted wedding and the predictable happily-ever-after.

Dunne, always a joy to watch, does his very best even when the material fails him (he has, for example, a very funny, utterly random bit freaking out in the back of a cab). He’s supposed to be the straight man, but his reaction shots and dialogue (“Are you the Antichrist? You can tell me, I won’t be mad”) garner most of the picture’s laughs. Madonna does herself no favors by adopting an exaggerated accent and inflated sexy-baby voice, but she looks fierce, takes no shit (“DON’T YOU SHUSH ME! NOBODY IGNORES NIKKI FINN!”), and has her moments; there’s a great throwaway line, during the climactic big fight, where she sing-songs a “Hurry up, I’m bored!” to Loudon as she skips around, chewing on a hunk of wedding cake.

It’s not really a good performance, per se, but it’s an energetic one, and that kind of goes for the movie too. They’re going for a “madcap” vibe that sometimes lands and sometimes just sweats desperately, but Who’s That Girl is so eager to please, it ends up being a very hard movie to hate. Sure, it’s formulaic and overcooked, but it’s ultimately a pretty typical ‘80s comedy, no better or worse than average, and most likely over-scorned at the time due to the Madonna-movie-failure narrative. (It’s certainly better than, say, a hit like Mannequin.)

Look, we’re not talking about an overlooked treasure here. But Who’s That Girl was one of those movies that got quite a bit of late-‘80s HBO airtime, and I’ve always recalled it with a fondness easily chalked up to both shabby pre-teen taste and understandable pre-teen Madonna crush. Revisiting it for this column, for the first time since then, its flaws were more apparent. But it still has its charms.

“Who’s That Girl” is available for rental or purchase via Amazon, iTunes, and the usual suspects.