Bad Movie Night: Madonna and Sean Penn’s Famous Flop ‘Shanghai Surprise’

To commemorate the thirtieth anniversary of its theatrical release, we look back at the movie that sank Madonna's big-screen ambitions.

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 thirtieth anniversary of its theatrical release, we take a look back at the movie that sank Madonna’s big-screen ambitions, and perhaps her first marriage, Shanghai Surprise.

If you didn’t live through it, it’s hard to fully grasp how much of a tabloid sensation the courtship and marriage of Madonna and Sean Penn was. For watchers of the entertainment media – then beginning to cross over from the disreputable likes of the National Enquirer to television shows like Entertainment Weekly – the Madge/Penn union offered up something for everyone: the whirlwind romance of two of the hottest stars in the fields of music and film, the merging of a material girl and a bad boy (one prone to punching out paparazzi, bonus), the quick reports of trouble in paradise, an acrimonious annulment and divorce. Smack in the middle of all that came 1986’s Shanghai Surprise, an adventure/romance that teamed up the off-screen spouses for an onscreen round of “first they hate each other, then they love each other.” It should’ve benefited from the overwhelming interest in the power couple; it should’ve allowed Madonna the opportunity to further extend her multimedia empire into film. Trouble was, they made a lousy movie, and she was lousy in it, and nobody came.

Occasionally, in perusing the pictures that make up this column, one encounters a project that could’ve worked, had it just gone a smidge in another direction (we just had one of those a couple of weeks ago). This is not one of those cases. Watching this flat, lifeless, bloodless adaptation of Tony Kenrick’s 1978 novel Faraday’s Flowers, it’s hard to imagine what attracted any of these players to this material – aside from the presumption that if Sean Penn and Madonna wanted to make this movie together, it must be worth making. It feels, more than anything, like the duo went looking for a movie they could co-star in, and this was the only script that was lying around.

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The setting, per the on-screen titles, is “Shanghai 1937: The Year of Japanese Occupation.” In a brief prologue, we’re introduced to the picture’s McGuffin: the “Faraday’s flowers” of the original novel’s title, a giant shipment of potent opium that is swiped from British baddie Walter Faraday (Paul Freeman) by sneering Japanese villains as he attempts to flee the country. Flash forward to a year later, as con man Glendon Wasey (Penn) is recruited by missionary nurse Gloria Tatlock (Madonna) (yes, as a missionary nurse) (yes, really) to guide her into the Shanghai underworld to track down the shipment, which she hopes to use as opium for sick children or something. Of course, they’re not the only ones looking for Faraday’s flowers, and intrigue and complications ensue, etc. etc. etc.

Shanghai Surprise runs 97 minutes, and it’s not just that it feels longer – it feels like it’s supposed to be longer, like a 115-minute movie that was clumsily truncated when MGM realized they had a clunker on their hands. You can feel the phantoms limbs of missing scenes all over it, particularly in the case of Penn, who is introduced as though we already know him, and this is merely the latest adventure of our charming rogue hero. Suffice it to say, this does not turn out to be Penn’s wheelhouse; he does a lot of things well as an actor, but wielding a light touch is not one of them, and when he dispenses wiseguy quips like “He blinked a few times, blew a few smoke rings, and whistled a mean chorus of ‘Beat Me Daddy’ eight to the bar,” he just can’t toss it off. Cary Grant couldn’t do Brando roles, sure – but the opposite was also true.

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In all fairness, he’s done no favors by the movie around him. Its portrait of the Shanghai underworld plays like a 97-minute explainer of Orientalism, all opium dens and exotic concubines and gangsters who speak in broken English (“Joe Go very very sorry about bump on head, but just pretend it was wild pitch”). And that style unfortunately extends to the work of Mr. George Harrison; what can I tell you, bad movies make for strange bedfellows. Harrison co-produced the movie via his Handmade Films shingle – their more esteemed productions included Monty Python’s Life of Brian, The Long Good Friday, Time Bandits, and Withnail and I – as well as co-writing the score (with Michael Kamen) and writing and performing several original songs. But from the gong and vaguely Asian theme of the opening song on, his score is barely more sophisticated than the hack plinking that used to greet the entrance of Asian sitcom characters. And this was also not exactly his most creatively inspiring period, as seen in lyrical couplets like “You could be kinder / and show me Asia minor” and “I’m not sure what’s in your eyes / mmm, Shanghai surprise.”

At the time of its release, Harrison’s involvement was a big hook for Shanghai Surprise – “Ex-Beatle George Harrison Takes on a New Challenge as Madonna’s Tough Movie Boss,” reported People. But Harrison mostly found himself trying to keep the press at bay, in light of breathless reports of turmoil from the movie’s set. It’s important to remember, in reading that coverage, how much was at stake for Madonna here; she’d received praise for her film debut the previous year, a supporting role in Susan Seidelman’s wonderful Desperately Seeking Susan, so this was her chance to prove herself as an honest-to-goodness actress/leading lady.

Considering the pressure she was under, and the breezy brilliance of her Susan turn, it’s all the more disappointing that she’s so bad in Shanghai Surprise. But make no mistake about it: she is baaaaad. From her first scene, rolling her eyes and pulling faces and sneering “Mr. Burns, you can’t be serious” at the suggestion of the team-up, she’s overdoing the theatrics, and when she gets tough with Penn, barking, “I do not intend to be made a fool of – you’re flippant, facetious, and, I suspect, sorely lacking in moral fiber,” the stiffness of the line readings betrays her discomfort.

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Put simply, she’s woefully miscast – we don’t buy Madonna as a goody two-shoes missionary nurse, or as ‘30s ingénue (she whines “Misss-ter Wayyyze” as if he’s the mall security guard). The key to the performance lies in the scene where, to get Wasey to further pursue the opium, she seduces him. It’s a scene that should play for laughs, the innocent pleading, “You’ve got to help me, you’ve just got to,” before determinedly disrobing. But when she tells him, “You leave me no opportunity but to put you under obligation,” she can’t resist putting her buzzsaw purr on it, which torpedoes the entire scene; the way she says “put you under obligation,” it sounds like (frankly hot) kink, something out of a dirty talk break on “Justify My Love” or “Erotica.”

It’s not hard to guess what happened here. Madonna, as a screen performer, had endless charisma but fixed range. There’s not a thing wrong with that;  you can make a case that her idol Marilyn Monroe was cut from the same cloth. But Penn was her opposite, a chameleon who disappeared into each character, and rarely displayed much personality outside of those characters. It seems clear that when given the opportunity to share the screen with him, she wanted to be his kind of performer, instead of hers; you feel her trying to show her versatility, and instead showing her limitations.

Shanghai Surprise’s equally dreadful reviews and box office basically put the kibosh on Madonna’s big-screen aspirations (though it certainly didn’t seem to do Penn any harm; make of that what you will). It erased Susan with a new conventional wisdom that Madonna was not only a bad actress but box-office poison, a notion confirmed by the similar receptions to 1987’s Who’s That Girl and 1989’s Bloodhounds of Broadway. She finally managed a course correction with her supporting role in Dick Tracy, but by then, it was too late – she would subsequently only find cinematic success in supporting roles (like Tracy and A League of their Own) or when playing herself, either literally or figuratively. And from this point, thirty years hence, Shanghai Surprise plays mostly as a dull miscalculation, at a point when, as a film performer, Madonna couldn’t afford one.

Shanghai Surprise isn’t streaming anywhere. You have to buy it, or find a video store. Good luck!