Where did I leave off? Oh yes, Goodfellas.
Ok, so here are my recommendations for the 90s and 2000s, in no particular order:
King of New York
Christopher Walken stars alongside Lawrence Fishburne and Welsey Snipes in this excellent film that fits nicely into the gangster sub-genre known as "return of the big shot." Last time I talked about Key Largo, one of the earliest in the genre. These are movies where a gangster who is past his prime and tries to come back and rise to the top again. In this movie, Frank White comes out of a 25 year sentence and finds his city falling apart due to the baseless morals of those that took his place (coincidentally, the Puerto Ricans, the "Asians" and the Italians). Yes, Frank WHITE comes to take the city back and put in place a gang operation centered around things like investing in hospitals. But Walken plays the character so well, you just gotta love his kooky movements and body language.
Also, two of the ruthless body guards in this movie are hot ladies.
New Jack City (1991)
1991 was a big year for African American filmmakers. More films featuring African American casts and directors came out that year than had during the entire Blaxploitation era. One of them was New Jack City, which took a lot stylistically from the classic gangster films of the past. Instead of rum running, gambling, or cocaine, this film focuses on crack cocaine. One thing I've noticed about films past 1980 is that they tend to give voice to the gangster's perspective in new ways. Before then, a lot of them got lectured by authority figures in the end or during conversations with the cops trying to bring them down. Now, we see a lot of gangsters talking about why they do what they do, the limited chocies they've had, and that they see themselves as no more ruthless or immoral than other businessmen.
Carlito's Way
You gotta love anything with Carlos Guzman. He can play anything. ANYTHING. True, he does usually play Puerto Rican gangsters or Puerto Rican gay dudes. But give him Hamlet and he'd kill it, I bet.
Anyway, did you like Al Pacino as a cuban gangster? Well get ready for Pacino as a Puerto Rican gangster. Carlito Brigante gets out of prison and wants to stay on the right side of the law, but his past life keeps bringing him back in.
Pulp Fiction (1993)
Finally, we're leaving New York for a minute. I saw this in high school, and was so into it I saw it 3 or 4 times in the theater! You're wondering if you should see it since it's been so long and maybe it isn't relevant. See it. It's set in Los Angeles. The story structure is interesting, the characters are fascinating, and I like the way it introduces the gangster in a different way. Sure, we see a mob boss type character for part of the film (a very disturbing part), but it's Jules and Vincent that steal the show for me here. Two gangsters with different world views, one of whom does something gangsters in these movies just doesn't really get to do: find a way out and some kind of redemption.
Reservoir Dogs (1991)
Tarantino has a way with an LA story, and if he'd just not cast himself in every film (and thus annoy me to no end), he'd make far superior movies. This one is a great example of a postmodern gangster film, where the characters reference and understand the gangster genre and have conversations about all kinds of stuff, including the benefits of tipping, and the metaphorical meaning behind Madonna's "Like a Virgin."
Boyz N the Hood
I'm obviously trying to represent for the west coast here. But hell, so many movies are about New York, it's nice to see an examination of Los Angeles gangs, especially during an era where Los Angeles gangs were spiraling out of control. It explores the pressures young men in inner cities deal with, and the cycle of violence that plagues communities that are allowed to decay by an uncaring system.
A good film, but a much more interesting examination of the period, it's history, and it's legacy is Stacy Peralta's documentary Crips and Bloods: Made in America.
American Gangster
Did you not see this? It's good. Very good. Well, I have some problems with the ending, but it's nice to see Frank Lucas represented in the genre. Lucas gets pure heroin shipped into America during the Vietnam War era via military service planes in the coffins of dead soldiers. Yeah. I know. He sees himself as a community hero, as someone who takes care of a community (and his family) when no one else will. And there's this other stuff with Russel Crowe's character that I'm not into, but see it. Did you know that you can't just rub a stain on an alpaca rug, you have to blot? These are cleaning tips I needed to know.
The next three are Scorcese's contributions:
The Departed
Even though Jack Nicholson is hammy and ridiculous, the story and the Damon/DiCaprio dynamic is excellent. Also, see the movie just for Mark Wahlberg's character. He's my personal hero after this. Well, the character is. The real Mark Wahlberg strikes me as kind of a douche. Like, he can't handle it when people refer to "Marky Mark." Dude, you made up that lame ass name! Also, his making fun of Andy Samberg's nose strikes me as quasi-nazi. Speaking of that:
Gets me every time.
Casino (1995)
I don't know why this isn't my favorite movie. It's a gangster film based in Las Vegas. How is not? It may not be my fave, but it's up there for sure. Based on true events centered around the now (sadly) demolished Stardust casino, we get a birds eye view of how the mob functioned in Vegas. Excellent work by De Niro, of course, but I was really fascinated by Sharon Stone, who pulled out all the stops for her character. Scorcese is hit and miss when it comes to female characters, but I think hers was a nuanced, complex role worth seeing.
Gangs of New York (2002)
Saved the best for last, right?Gangs of New York is set in New York, but it's much earlier than any of the gangster films that came before it. We're talking during the Civil War era, when the city was dominated by mobs and political bosses. Lower Manhattan's "five points" area is at the center of another war, "natives" vs. immigrants. The Natives are led by Bill The Butcher Cutting, played by Daniel Day-Lewis. Amazing role. Lewis left his acting retirement for this role. And he wasn't like hanging out in Miami wondering what he was going to do without filmmaking. He was a cobbler in Italy. Dude just up and started a new life as a cobbler. And he said, damn, I have to play Bill the Butcher. You should see it just for that, but also for the history lesson, the story telling.
Even though it's about 19th century gangsters, it explores what all gangster films do, the limited resources and options available to the poorest people in the nation, and the short-term thinking that usually leads people to get so focused on their own problems that they fail to see how larger forces are shaping their lives. That, more than bad morals, ultimately leads to the gangster's downfall.
Ok, that's enough for now. I know, I missed a bunch of favorites, like Millers Crossing, and I left out films I thought were part of other genres but still contained gangster characters, like heist films (Oceans 11, The Italian Job, etc.). And don't even think to include West Side Story in here.
Got any you wanna add?
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