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May 02, 2018 at 12:34 PM EDT

The summer of 2008 broke history, and rebuilt it. America suffered through a bitter presidential election on the road to a globewrecking financial crisis. In theaters, cinematic generations were rising — and falling. Superheroes, Will Smith, George Lucas, Guillermo del Toro, Emma Stone, Mike Myers, Sisterhoods and Step Brothers, Batman and ABBA, adaptations of TV shows we still tweet about, new installments of movie franchises studios won’t stop rebooting: Everything Hollywood was before, alongside everything it still is. In our weekly column Two Thousand Late, we’ll explore the big hits and curious flops from a summer that has never really ended.

So much depends upon rich, powerful, oversexed misogynists. They cause so many problems, true. But here’s a question you could ask: Can they also solve those problems they cause?

Ten years ago, on May 2, 2008, two movies about the redemption of identically awful men arrived in theaters. Iron Man was the one about Iron Man. Made of Honor was not about Iron Man. Dramatic pause: Or was it?

Consider. In Made of Honor, Patrick Dempsey plays Tom, a guy who has it all. In college, he invented the “coffee collar,” the cardboard sleeve for coffee on the go. This made him a millionaire, but he wasn’t poor before. His father is a quintuple-divorcé. (Or is it sextuple? Sex, LOL.) Played by Sydney Pollack in his final film role, Tom Sr. is the very model of the vintage Manhattan tycoon, that rarified stratosphere of movie-rich where his money is the whole joke. When we meet him, he’s negotiating a prenuptial agreement with his latest baby bride — on their wedding day, minutes before the ceremony. The negotiation comes down to: How often do they have to per week? “Have to” what? (Sex, LOL.)

Robert Downey Jr.’s Tony Stark was also, most immediately, a rich bro with daddy issues. He sums up his philosophy of war-profiteering arms manufacture: “I prefer the weapon you only have to fire once. That’s how Dad did it. That’s how America does it.” Funny stuff, when the point was establishing Tony Stark’s douchebag credentials. (And you have to briefly erase the following decade of continuity here, I think, all wars Civil or Infinity. Return to a lost-forever cultural moment before cinematic universes, when it felt like Iron Man was a most clearly movie about Malibu George W. Bush evolving into Heavy Metal Jon Stewart.)

Tony and Tom have another thing in common. These women: They never stop! Tom walks into Starbucks, and a woman writes her number on his coffee cup. He sits down, the woman at the next table smiles at him. This one woman hates him so much that she gets drunk and throws herself at him. Another woman loves him so much, she builds a website about him, AllThingsTom.org. “Her last blog was a two-page description of my face,” Tom tells us. (The blogger stalker has glasses, too, because the year is 2008 and nerds do computers.)

How irrepressible is he, our Tom? His best friend’s mom is mad when she sees him:

Best Friend’s Mom: “You slept with our maid!”

Tom: “I didn’t know she spoke English!”

Which is not the only line that sounds admissible in court. Made of Honor is a lazy movie. To convince you that Tom is a cool guy with lotsa ladies, it shows you scene after scene with lotsa ladies telling Tom he’s a cool guy. Iron Man is a very clever film, with lots of screenwriters, but most crucially Jon Favreau directing. So it can quickly explain everything about Tony Stark’s relationship to women in a single shot: Private jet, booze, flight attendants with bare midriffs, a slooowwly ascending stripper pole setting an impressive new benchmark for family-friendly phallic imagery:

Tony and Tom have one other thing in common. Womanizers? Yes. Cads who never call back? Sure. But they are redeemed by the devotion of one single trusted person. For Tony, it’s Pepper (Gwyneth Paltrow), his personal assistant, long-struggling yet witty bantering, the kind of trusty galpal who kicks last night’s galpal out of the house. For Tom, it’s Hannah (Michelle Monaghan), best friend since college, some kind of museum worker. They are our mens’ confessors, though more accurate to call them enablers. And I don’t want to say these movies specifically humiliate these characters as a running joke, but when Hannah is introduced working on a painting of Saint Sebastian, the camera framing is rather suggestive:

Lest you’re worrying this movie will be subtle, she proudly declares, “I just finished working on his balls!”

You know from the first minute where these men are going with these women. They’ll wind up in love: In male-female dynamics, romantic comedies and superhero movies build the same clockwork. The fact that Pepper is Tony’s subordinate is retroactively hilarious or sad, makes the cheerful tone of Iron Man feel like a #MeToo lullaby, a Love Song for the Old Days When You Could Just Flirt With Your Personal Assistant No Big Deal.

But some central idea of the Iron Man trilogy (and no other movie featuring Iron Man) is that Tony is basically a Hollywood executive who happens to work in tech. So you could describe these blurred lines as “documentary accuracy.” And it’s fun to see Paltrow banter with Downey, and one film later she was a CEO, so that’s one problem solved, I guess.

The way Tom meets Hannah is much weirder. Like maybe too many superhero movies, Iron Man earns extra credit for nominal topicality, but Made of Honor laps it for American-historical resonance in the very first scene. We open on a flashback to 1998, at Cornell. It’s a Halloween party, and Tom’s gone Full Bill Clinton, the mask, the voice, the randy attitude. Half the women at the party are dressed as Monica Lewinsky. (One woman’s wearing a Hillary mask, and I truly can’t remember how that gag played in May 2008, one month pre-concession. I think my theater audience groaned.)

But Tom’s looking for one special Monica. She gave him directions. He goes upstairs, walks into a dark dorm room. He takes off his clothes, and slides into bed next to a sleeping woman. Who isn’t the woman he thought it was — it’s Hannah! Meet-cute! “I gotta be so careful with who I get in bed with from now on,” says Tom, which is not the only line that sounds admissible in court.

Circa 2008, the Romantic Comedy was in a state of transition, what could feel like decay. Made of Honor mixes four divergent ideas about its own genre: Graceless imitation-Apatow vulgarity, mid-period Entourage bro-downery, this idea someone had around 2005 that men were suddenly less manly than they used to be, this idea someone had generations ago that Man and Woman can be friends without screwing (OR CAN THEY). It is, recognizably, a gender-swapped riff on My Best Friend’s Wedding: Hannah gets engaged, Tom realizes he loves her, and from there it’s all about wrecking the top pal’s nuptials. Gender-swapping a story to give more prominence to the male characters: In some ineffable way, this was the 2000s.

Circa 2008, by obvious comparison, the Superhero Movie was in genre ascension. So there has been, and will always be, much more written about Iron Man than the other big May 2 release. It is more convincingly the story of a bad man becoming better. Tony is wounded, imprisoned, realizes that manufacturing weapons often leads to those weapons doing what you build weapons for. Because Downey is giving such a great performance, because Favreau constructed such a playful origin riff, and because things only get boring in the final fight, you go along with the whole contraption. It’s convincing, which doesn’t equal honest. By the film’s end, Tony’s fixed all the problems that his company caused. The obvious follow-up question in any real-world scenario would be: What problems will they cause next? (By Iron Man 2, Tony was bragging about how he had “privatized world peace,” a line that would be Trumpian if Trump ever talked about peace.)

Tom doesn’t really learn any lessons. This makes Made of Honor a much worse movie, but you wonder if it’s also more honest about the mindset of the toxic narcissist. The film is unconvincing as a hero’s journey, and thus intensely convincing as a portrait of a villain who considers himself a hero.

Hannah asks Tom to be her maid of honor, and the movie thinks this is hilarious, because waitaminute, man-human cannot be maid-girl! Actual dialogue: “Did he just say he’s maid of honor? He’s a bloke!” Multiple characters think Tom must be gay, which is ho ho, because obviously so much lady-humans love Tom who is straight.

But he throws a pretty good bridal shower. And he studies all the essentials of wedding planning, and at one point random people actually applaud him in a department store. “You were amazing today,” Hannah tells him, and then she insists, “You’re always amazing.” There’s a running thing in the movie where even the dogs love Tom, and he loves all the dogs, treating them nicer than he treats his ornamental women.

The world loves him! And yet, he must change. “Maybe there’s more to life than just sleeping around,” he says early on. The dark joke of Made of Honor is how Tom’s pursuit of Hannah from there is purely destructive, an act of constant subterfuge. “I need to destroy the wedding from within,” he says. His bros encourage him, and together they chant: “Steal the bride! Steal the bride!”

I know, I know, romcom behavior, secretly sociopathic: Old joke. But Made of Honor feels special to me, an important snapshot. It throws out any sincere ideals of romantic love. Briefly, Tom considers letting his best friend get married. He quotes that old line: “When you love something, you have to let it go.”

“Said by a p—-,” his dad responds.

But what about Casablanca? Tom asks Daddy. Didn’t Bogie put his love on the plane for the greater good?

“P—-,” says Tom Senior, “Big p—-.”

A dumb joke, but resonant in a dumb movie. No such thing as old-fashioned values, says the Manhattan business millionaire, already working on his next divorce. Forget Bogart, says Pollack — the fact that this was Pollack’s last role makes that “p—-” line doubly sad, two fine generations of masculinity incinerated at once.

Hannah’s a distant figure in the movie. Not Michelle Monaghan’s fault: Character and actress look trapped. And look, it’s maybe too easy, post-Reckoning, to look at any older movie with fresh eyes, declaring: “Ah ha, here is a film whose meaning is opposite-good when, friends, you consider the facts of gender!”

But one scene pushes Made of Honor from the realm of merely dumb, makes it look like a prison built for the female lead. The night before her wedding, Hannah’s mom (Kathleen Quinlan) comes by her bedroom to look at old photos with her daughter. The memories start to flow. “I miss Dad so much,” says Hannah. This is first and only time we hear about her late father, and then the mom says: “He was always so convinced you were gonna marry Tom.”

Even her dead dad loves Tom! Moments like that, the fog lifts. You spot a vast male conspiracy all around Hannah, this man and his dad and her dad and all the men around her, STEAL THE BRIDE, STEAL THE BRIDE. Meanwhile, her relationship with Colin (Kevin McKidd) is lousy with century-old clichés of courtly love. They met six weeks ago, they’re engagement lasts two weeks. They barely know each other: She is shocked, shocked, to discover he enjoys hunting. As part of the wedding festivities, they engage in the old Scottish ritual of the Highland Games, all the women dressed up as lordly ladies, suggesting female archetypes almost as ancient as nerdy blogger-stalkers.

In the end, the prophecy of Hannah’s father has come true. The last scene of Made of Honor is in the marital bed. Tom turns on the lamp: “I’m just making sure I got the right girl this time.” Ho ho ho, hooray for old behavior unforgiven, huzzah for the cad who homewrecked his way toward his happy ending! “Oh, Monica,” he whispers to his wife. “Oh, Bill,” she whispers back, captured.

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