Here are numbers 19-16 coming at ya. Within these you will see read about films that deal with the Prohibition, a good cop/bad cop storyline, etc. There are a couple Oscar Winning films and two films from my favorite director of all time: Martin Scorsese. Check them out after the jump:
19. Gangs of New York (2002)-
The king of gangster films Martin Scorsese brought an interesting look to the genre in 2002. Gangs of New York is set in 1863 and shows the story of an Irish immigrant trying to get revenge on his father's murder. However, there is more to the story then just your stereotypical revenge story. This film shows the beginnings of what is now Manhattan and how the influx of immigrants in New York City helped shape the city it is today. 
In the film, we see Amsterdam Vallon (DiCaprio) returning to the "Five Points of America" (lower Manhattan in NYC) to seek vengence against his father's sadistic killer Bill "The Butcher" Cutting (Lewis). When he returns, Vallon sees that lower Manhattan is now run by several different gangs with The Butcher being the head of the most powerful (The Natives). Mixed into the story are the 1863 riots where working class men were required to be drafted into the Civil War with the wealthier men being spared from the draft.
This film is always being shown on AMC or IFC (was actually on 3 times this week). If you have a couple hours to kill (the film is long just like all Scorsese films) you will definitely want to check it out. It's not Goodfellas or Casino, but definitely deserves the number 19 spot on this list.
Famous Tagline: "America was born in the streets."
Trailer:
18. Miller's Crossing (1990)
One of my favorite films of all time (The Big Lewbowski) was written by The Coen Brothers. After I saw that film I wanted to check out more of their films including Fargo and Raising Arizona. However, I never knew about this film until a couple years ago and what a great find! Setting? The Prohibition during the 1930s. Mobsters ran everything from underground casinos and distilleries all over the US and Canada, to having government officials in the palm of their hands.
The film stars actors such as Gabriel Byrne (The Three Musketeers, In Treatment, The Usual Suspects), John Turtorro (The Big Lewbowski, State of Grace, O Brother, Where Art Thou?) and a young Steve Buscemi (Fargo, The Big Lewbowski, Resevoir Dogs, Boardwalk Empire) even has a small part. Tom Reagan (Byrne) is an advisor to a big-time crime boss. Regan gets caught up in a feud between his boss and another big-time crime boss. He tries to keep the peace between but in the end he gets caught in the cross hairs between the two bosses.
The story is your stereotypical Coens Brother film with a complex storyline. While watching this movie, you can tell that they really try to make it known to the viewer that it is set during the Prohibition. You need to pay attention to the film the whole time to be able to figure out what is going on within. If you like films with liquor, guns, and sex then this movie is for you.
Best Line:
Tom Reagan: "Tell Leo he's not god on the throne, he's just a cheap political boss with more hair tonic than brains."
Trailer:
17. Training Day (2001)
I think the best actors of all time include greats like Robert DeNiro, Al Pacino, Jack Nicholson, and you can definitely add Denzel Washington (Philadelphia, John Q, American Gangster) to that list. Compared to all of the films he has done in his career, Training Day is one that stands out to everybody. In Training Day, Denzel gives one of the best performances (alongside a performance from a film later in this list) he has ever done in his career (which in turn earned him the oscar Best Actor for that year). Along with his partner in the film Ethan Hawke (Dead Poet's Society, Gattaca, Before Sunset), they put together a great on-screen team.
Jake Hoyt (Hawke) is a rookie cop who is starting his first day on the job as a narcotics officer. He is assigned to work with his new partner Detective Alonzo Harris (Washington). Throughout the movie you see that Harris isn't really the kind of cop Hoyt learned how to be. As the film progresses, the story gets darker and darker. With Hoyt on his first day of on the job training, he needs to decide whether or not to go the rout of being a bad cop like his new partner that has gangster intentions or be the good cop by abiding and enforcing the law he was taught. In the end, he only has 24 hours to make his choice. Best Line:
"Alonzo: What's that?
Blue: Motherfucking crack, man.
Alonzo: That's right, Jimmy Crack Corn. 1, 2, 3, 4, 5, 6. Oh, you're federally fucked now. You got crack... and a gun. You know with your record you can get 10 years per bullet? Now you gon' gimme a name."
Trailer:
16. The Departed (2006)-
As you will see throughout this list, Martin Scorsese has numerous films that were more than deserving to be on it (this is why when someone asks me who my favorite director of all time is I will always say his name). When I heard that for Scorsese's next film he was going to be doing another gangster-esque film, words can't describe how excited I was. A couple years earlier he put out The Aviator which was a great film but the plot didn't have anything to do with the mafia or gangsters. Prior to The Aviator, Gangs of New York was released. Gangs of New York (which was again a great film) was missing something. I don't know what it was but it definitely wasn't up to par with Goodfellas and/or Casino. The Departed had everything Gangs of New York was missing and then some.
Returning to work with Scorsese again was Leonardo DeCaprio (Gangs of New York, The Aviator, Shutter Island) and Alec Baldwin (The Aviator, Beetlejuice, 30 Rock). The film also starred Jack Nicholson (Chinatown, Batman, One Flew Over The Cuckoo's Nest, The Shining), Martin Sheen (Apocalypse Now, The West Wing), Mark Wahlberg (Boogie Nights, The Fighter, Four Brothers), and Matt Damon (Good Will Hunting, The Bourne Trilogy, Rounders). This movie gave Scorsese's first Oscar for Best Director (as hard as it is to believe with films like Raging Bull, Taxi Driver, Goodfellas and Casino under his belt) and also won Best Picture of the Year. The film takes place in South Boston. The state police force is gunning down on the Irish-American mafia led by Frank Costello (Nicholson). However, Frank Costello has someone working in the "staties" who has been a long time close friend. Colin Sullivan (Damon) is introduced to Frank Costello when he was just a little boy. He grew up very close to Costello and when he becomes a Massachusets State Policeman Costello is even there at his graduation and informs him "school's out".
With Costello having a mole inside the staties now it's the State Police's turn to have a mole inside Costello's clan. Billy Costegan (DeCaprio) goes undercover to infiltrate the Costello's operation. As he is undercover nobody in the State Police know that he is undercover. However, once Frank Costello figures out someone in his crew is an undercover cop he has Sullivan try to find out who it is. The race is on between Sullivan finding out who is undercover in Costello's outfit and Costegan finding out who is the mole in the State Police. This movie has several twists and turns that will leave you shocked. There are a lot of "WTF?!" moments that will make you love every minute of this film.
Best Line(s):
1. Frank Costello:Who let this IRA motherfucker in my bar?
[the man looks startled] Frank Costello: [laughs] Only kidding. How's your mother?
Man in Costello's Bar: Oh... I'm afraid she's on her way out.
Frank Costello: [walks away] We all are. Act accordingly.
2. Frank Costello: When you decide to be something, you can be it. That's what they don't tell you in the church. When I was your age they would say we can become cops, or criminals. Today, what I'm saying to you is this: when you're facing a loaded gun, what's the difference?
3. Billy Costigan:[to the bartender] Cranberry juice.
Man Glassed in Bar: It's a natural diuretic. My girlfriend drinks it when she's got her period. What, do you got your period?
[Billy grabs an empty glass and smashes it onto the man's head.]
[Billy grabs an empty glass and smashes it onto the man's head.]
Trailer:
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