The core of what we might call the "Elmore Leonard Cinematic Universe" is Quentin Tarantino's Jackie Brown (1997) and Steven Soderbergh's Out of Sight (1998), which adapt the Leonard novels Rum Punch (1992) and Out of Sight (1996). Both films include the character of Ray Nicolet played by Michael Keaton. Then you have the movie Life of Crime (2013) by Daniel Schechter, which adapts The Switch (1978). Rum Punch was a sequel to The Switch, so Life of Crime is essentially a prequel to Jackie Brown, showing the characters of Ordell Robbie, Louis Gara, and Melanie Ralston twenty years younger.
Jackie Brown is about a flight attendant and occasional drug smuggler (Pam Grier's Jackie Brown) who gets pulled into an ATF sting operation against career criminal Ordell Robbie (Samuel Jackson). Michael Keaton's Ray Nicolet is one of the law enforcement officers pressuring Jackie to do this, a kind of goofy guy who's always moving around and sitting in odd positions:
Ray Nicolet reappears in Out of Sight, now working for the FBI, in a romantic relationship with the film's female protagonist, Karen Sisco (Jennifer Lopez). Ray is married, but Karen is going out with him anyway, much to her father's disappointment. It doesn't last long, though, because Karen soon falls for bank robber Jack Foley (George Clooney). Ray's definitely the same kind of goofy guy; my favorite scene is when Karen's dad makes a sarcastic comment about the subtlety of his "FBI" t-shirt, asking if he has one that says "undercover" too.
Ray doesn't get it, just going "huh?"
It's not a big connection, but it is a nice one, I think. Keaton made the appearance in Out of Sight uncredited; he was apparently very enthused about it: "I thought that was the coolest idea [...]. I said, 'I'll do it. But you have to do one thing: You have to make sure he is that guy.' There has to be something in the wardrobe that you go, Oh, there he is again! 'Cause I wanted the people to be sitting in the theatre going, 'Oh, I might see him at the Dairy Queen later, like he's a real guy out there wandering around in life. Then he might pop up in another movie. He might be down at the mall!'"
Jackie Brown might not know Karen Sisco, but you know they both could meet, because they both met Ray Nicolet. It's like how before The Avengers came out, Iron Man might not have met Thor, but you knew they could meet because both men knew Agent Coulson. (A little confusingly, though, Samuel Jackson also appears in both films, but as a different character in Out of Sight than Jackie Brown.)
Life of Crime came out fifteen years after Jackie Brown, but is set twenty years earlier. The two films aren't officially connected, but the books they're based on are. Mos Def plays the young Ordell, John Hawkes the young Louis (Robert De Niro in Jackie Brown), and Isla Fisher the young Melanie (Bridget Fonda in Jackie Brown). Ordell and Louis are criminals who kidnap Mickey Dawson (Jennifer Aniston) to extract ransom money from her husband.
I actually think Mos Def was doing a little bit of Samuel Jackson with his voice. It's not an imitation or anything, but it would come through on occasion. You can definitely see how 1970s Ordell would become 1990s Ordell. He's already a little ruthless in Life of Crime, though it seems like he hasn't actually killed anyone before. He has big aspirations, however, and of the two men, he's the one more inclined to go through with them. With twenty years of success, Mos Def's more reserved character could evolve into Jackson's more over-the-top one.
Louis was an old criminal friend of Ordell's who had just gotten out of jail at the beginning of Jackie Brown. In Life of Crime, he's a criminal, but definitely naïve. At the beginning of Life of Crime, he gets robbed in a bar restroom; later in the film, he falls for his kidnap victim. Other than Mickey, he's the character you sympathize with the most in Life of Crime, and thus there's an extra layer of tragedy if you've seen Jackie Brown, because you know he's going to end up burnt out, hopeless, with severe anger issues. Given how likeable Louis is, it gives a little bit of frisson to his sporadic attempts to do the right thing in Life of Crime.
The transition between Isla Fisher and Bridget Fonda as Melanie is the hardest to buy. She's Mickey's husband's mistress in Life of Crime, and one of Ordell's girlfriends in Jackie Brown (though she hooks up with Louis). The ages don't line up, as Fonda is too young to have been an adult in 1978 (she would have been just fourteen*). Fonda's Melanie is stoned and disaffected; Fisher's Melanie is more active and conniving. Though both have the apparent catchphrase of "Wanna fuck?" It's hard to believe Melanie would end up with Ordell after the events of Life of Crime, or that Louis would want to have sex with her, though I guess it goes down that way in the books.
I guess there are twenty years between the two films, even if Melanie somehow de-ages by four. But it's pretty clear in Jackie Brown that Louis and Melanie have never met before.
What unites the three films is more than a continuity of character, though. All three films, even though they're from different directors, have a similar tone, with bizarre, eccentric characters committing crime badly, and a pleasing mix of violence and comedy. There's always something to laugh at-- but there's always someone to root for too, on both sides of the law. We want to see Jackie Brown, Tom Foley, and Louis Gara get away with it. Plus there's awful people to root against. (I was a big fan of the neo-Nazi in Life of Crime for that reason. What happens to him in the end is glorious.) I suspect if you hadn't been told, and Ray wasn't in the films, you could still work out that Jackie Brown and Out of Sight came from similar source material. (I'm less sure about Life of Crime; it is less sharply directed than the other two.)
We enjoyed all three, though Jackie Brown felt like it could have been tightened, and I don't think Life of Crime was as funny as the other two. (It did have an absolutely amazing ending, though.) But Out of Sight was excellent, with a strong-as-always performance from George Clooney, and the best performance I've seen Jennifer Lopez give. The scene where they have drinks together is something else.
Recently, a YouTube video did the rounds where the maker claims that certain historical movies work well together if you view them as a "cinematic universe" à la Marvel. It's not as bad as most YouTube-based criticism; I liked his overall point that there's something neat about seeing the same events and the same characters filtered through the sensibilities of different directors and the conventions of different genres. What's interesting about the Elmore Leonard Cinematic Universe is that you kind of get both. These are similar novels filtered through distinct directors to come out with something similar again. A nice little unofficial trilogy.
* Actually, there's a scene in Jackie Brown where Louis looks at a 1976 photo of Melanie, and she says she's fourteen in it.
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