Fleeing from a botched robbery in toy store, Harry Lockhart (Robert Downey Jr.) stumbled into an audition to play a private investigator in a movie. Grief-stricken that his friend got shot by some lady determined to defend the sanctity of a toy store's Christmas product, he gave a bravura performance and won the role. Now he's in Los Angeles, getting tips from a real private investigator everyone calls Gay Perry (Val Kilmer), and running into Harmony (Michelle Monaghan), a childhood friend he had a huge crush on.
The case Harry accompanies Perry on ends up with a car in a lake, a dead body in the trunk. Harmony's sister turns up dead, an apparent suicide, though Harmony is convinced otherwise, given she was the one who hired Perry for the case with the body in the trunk. A body which soon turns up in Harry's hotel bathroom.
Harry reconnects with Harmony, fucks it up, tries to to fix it by lying, pisses off Perry, loses a finger, gets it back, sort of fixes things with Harmony, loses the finger again, fixes things with Perry, and ends up shooting a lot of people.
Harry is a creature of the moment. Part of that is he thinks he's clever, although this movie is full of people who think they're constantly making the wittiest comments imaginable. Sometimes they're even right. But he really just acts, in whatever way his emotions seem to dictate that moment. This is a guy who thought trying to rob a toy store to find a particular gift for a kid was a good idea, and when it went wrong, hid in an audition without knowing that's what he was doing.
He throws Perry's gun in the lake without stopping to check whether that's a good idea or not (it isn't.) He's got a lot of bitterness about women, and unleashes a spiel about how women who fuck a lot of guys all have fucked-up pasts, saying this to Harmony, who does, in fact, have a fucked-up past. He's impatient for answers, so he's tries the Russian Roulette interrogation technique on a hired killer, without being able to do basic math.
The, 'It was like an eight percent chance. Eight percent?! Who taught you math?!' exchange was one of those bits that I found as clever as the movie surely thought it was. Point is, Harry never really thinks before he does anything. The thinking comes after, when he has to reflect on how he's messed things up again. And maybe it works out. The final shootout, stationed on and under an overpass, involving a coffin, feels like a situation where Harry is simply reacting. He didn't really plan anything, because there was no time. He just did things, and it worked out. Maybe because it was actions and not words. He didn't have time to say something stupid that could ruin everything.
So it's a pretty good role for Robert Downey Jr. He can play a glib smartass in his sleep, but he's also good at the grief-stricken moments, and these moments of mostly impotent rage. Where's he mad, but he can't really do anything except spout more shit which is likely only going to make things worse. Or he has to backpedal instantly, as when he gets angry enough at Perry to snatch his sunglasses, but picks them off the ground and returns them the moment Perry tells him to.
Monaghan plays Harmony as simultaneously more grounded than Harry, but also more prone to getting blinders on. Harry tends to judge, quickly and harshly, off first impressions of what he thinks is happening. Harmony has actually lived in L.A. for a while, so she actually knows people and what they're like. There's a weary acceptance to her, except when it comes to something personal, like her sister. She has a dry wit, more controlled than Harry's. She picks her spots. She's not grief-stricken over her sister constantly, because she's angry, and she's also trying to decide what to do with Harry. The banter is easy between them, until Harry lets the wrong impulse control his mouth.
But she's also the one most likely to charge ahead without thinking. Harmony's the one that drives the plot, because she's the one convinced her sister was murdered. Harry plays along because he wants to stay close to her, presumably in the hopes he'll get out of the Friend Zone this time. His digging, done to impress Harmony, combines with the work she's doing, to drag Perry back in, largely against his will.
Kilmer's the alternately composed and frustrated center the other two whirl around like untrained puppies on leashes. He actually knows this work, knows how things usually work, knows what things a person should and shouldn't do, as well as what people are likely to do. Like, if they put a murder victim in your bathroom, they probably also phoned in a complaint to the cops. It makes him a bit of an exposition device at times - albeit one delivering exposition with biting commentary - but also keeps the plot moving forward at points the other two would hit dead ends.
It's a funny movie at times, but the plot's overly convoluted. You got daughters, fake daughters, assumed daughters. I didn't really even bother to try and keep track of everything. It's a film more about the style than the substance. There are multiple cases, they're connected. Everybody stands around saying clever lines, or trying to, and some people get shot. Harry's a little dazed the first time he kills someone, though that might be more about the person he let die just prior. By the end, he barely seems to notice how many people he shoots. They're just a body count.
Given that Harry narrates the story, I'd worry about an unreliable narrator, but he's so bad at it - forgetting to explain who people we see in flashbacks actually are - I don't think he could manage to embellish the truth if he wanted.
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