I am a big fan of movies about the mob. In creating this top 5 list, I had to determine whether I would add comedies. I decided against it, so let me quickly mention a couple of my favorite mob comedies:
Analyze This / Analyze That – Billy Crystal and Robert Deniro star in a film about a mob boss dealing with anxiety and depression. The premise of the movie is just funny in itself, but the delivery of the story really puts it over the top.
Mickey Blue Eyes – Hugh Grant is a high society Brit marrying into an Italian mob family, and somehow he gets mixed up in the business. I love it!
And now for the real Top 5 Mob Films…
Honorable Mention:
The Godfather Part III – The saga continues with Michael Corleone as an aging and more legit business man. The problem is that he couldn’t quite get the family out of the mob business. Michael’s illegitimate nephew from his brother Santino’s affairs is taking over the biz and fooling around with his cousin as well. This wasn’t a bad movie, it just lacked the superiority of the first two and suffered from unrealistically high expectations.
Casino – De Niro, Pesci, James Wood and Sharon Stone star in a movie about the dirty business that goes on in Vegas. It’s a given that this film would have a lot of brutal violence in it because the director is Martin Scorsese. There is not enough violence that could quench his appetite.
#5. The Untouchables – This is one of the few Brian De Palma movies that I like. Sean Connery, Kevin Costner (Elliot Ness) and Robert De Niro (Al Capone) star in this movie which is based on the true story of Al Capone and the men who brought him down on charges of tax evasion. De Palma is usually too “stylish” in his direction and editing for my liking, but I really like the way this movie flows.
#4. Goodfellas – Robert De Niro, Ray Liotta, Joe Pesci and Paul Sorvino beat up and/or kill just about everyone they can in this “based on a true story” movie about the drug dealing, fast living and ultimately tragic end that faces members of organized crime. Just remember, you never kill a made man. It never works out for you.
#3. Once Upon a Time in America – Composer Enio Morricone teams up with Italian film directing great Sergio Leone to frame one of the greatest movies ever made, much less one of the greatest mob films. De Niro, Pesci, James Wood and Elizabeth McGovern star in this movie about a Jewish mob in New York in the prohibition era and afterward. This is an extremely long movie with some harsh content, so be warned. The music and atmosphere this movie sets to me is just unbelievably good. Like most mob films, the themes of honor, family, betrayal, regret and finally destruction are all present. This movie is pretty deep, so pay attention.
#1 and #2 (tie) The Godfather and The Godfather: Part II – Marlon Brando, James Caan, Robert Duval, Al Pacino and Robert De Niro star in the greatest piece of American film art ever created. These two movies are almost seemlessly one movie. It follows the life of Vito Andolini from the town of Corleone. His father, brother, and mother were killed in Sicili by a local mafia chief, he flees to the US where he gets involved in organized crime and finally his family grows large enough to expand to Nevada gaming. The music is brilliant, the storyline is captivating and the film itself is rich and beautiful. The biggest themes of this movie are loyalty, honor, power, corruption, family, betrayal, and destruction. The heartbreak and disloyalty against Michael by his own people and his own family leads him to kill his own brother. The hotheadedness of Santino costs him his own life. The foolishness and naiavity of Fredo brings the whole family crashing down. Ultimitely, the story is about how the desire for power corrupts even the best of us.
The Citizen Cane 
Shouldn’t “On The Waterfront” at least get an honorable mention?
It was a Marlon Brando classic before all the mafia were stylish. They will not make a movie again that portrays union corruption/mob association in a mainstream Hollywood production with a mega-star leading man
” I coulda had class. I coulda been a contender.”
On the Waterfront is one of the great movies of all time, and had it been considered for this list it would have made the top five just after Once Upon a Time in America (OUTA). I didn’t consider it a mob flick because it was not so much in the La Familia, La Cosa Nostra, stylized mafioso type of film like the others. Even though OUTA was about a Jewish mafia, it was very mob style. You could make a legit argument for Waterfront, though.
Great review, Phillip—you’re right on the nose—GF 3 would have snuck in at least for a tie for #5 had Francis Ford Coppola not casted his daughter as Michael Corleone’s daughter–ironically, the background of the movie was true as there was a Vatican financial scandal in the late 70’s….
Vic, same with the parts 1 and 2 backgrounds. The scandals, the congressional hearings, the drug trade, and the gaming scandals were all part of what made this movie feel so real. I don’t think I’ll ever get tired of watching the Godfather saga. FF Coppola’s daughter almost ruined the movie. It also suffered from Pacino’s age because he seemed nothing like the old Michael Corleone. For some reason, they made him a much nicer, warmer father and kind Don Michael Corleone than the cold and detatched and sometimes explosively angry younger Don Michael Corleone.
It’s funny how many times James Wood, Joe Pesci, and especially Robert De Niro pop up in great mob movies. De Niro has to be the Hollywood mafia king.
Agreed