The 10 Best Gangster Movies and Films of All Time

The transition from VHS to DVD has been a difficult one for me. I have a lot of movies in my VHS collection. DVD is so clean and amazing, but I spent all those years building my movie library, now I gotta buy them all over again. Grrrr.... So, to upgrade a movie from VHS to DVD means I'm loving it. Here are the top 10 Gangster films that are part of my DVD collection or have been "upgraded."

This not only is a great story, but this film is well acted and well directed. Originally released in 2002 and directed by Sam Mendes of American Beauty fame, this tale of fathers trying to save their sons from the sins of the father weaves itself into and under your skin.

Brilliant performances by Tom Hanks, Paul Newman, Daniel Craig and Jude Law. There isn't one poor performance in this film. Road to Perdition was well cast, to say the least.

Visually, they have done well to recreate Illinios in this Great Depression drama that shows us the private lives of the Irish Mob at the end of Prohibition.

Based on a graphic novel, Road to Perdition will pull you in and keep you there.

Released in 1991 and directed by Barry Levinson, Bugsy gives us an inside look into the real life character on Benjamin "Bugsy" Siegal. Warren Beatty plays Siegal and we watch as this gangster from the old-school falls in love with the glamor of Hollywood and then sets his sites on a dream; Las Vegas.

Nominated for ten Academy Awards and winning two, Bugsy is a well crafted film that transports you right into the post war 1940s. Beatty's performance of Siegal is enjoyable and he seems to capture the visionary aspect of the character.  He also finds ways on many levels to bring a touch of humanity to an otherwise narcissistic, psychopathic man.

Anette Benning is simply fantastic as Virginia Hill. Whether or not this is how the real Virginia Hill acted or behaved in real life is beyond me, but she plays it brilliantly. As an actress, she held nothing back.

Also played well was Harvey Keitel as Mickey Cohen and Ben Kingsley as Meyer Lansky.

Bugsy is a great movie for time traveling in color.

What else can you say about a movie where the main character ends an argument by grinding a grapefruit in a women's face?

This was the movie that pretty much launched James Cagney. It came out in 1931 and tells the story of a young hooligan who rises to the top of the Chicago mob and carries with it the old adage that crime doesn't pay.

Classic 1930s film making. Incredibly fun to watch. The Public Enemy is one of those movies that is always great to watch on a rainy day or when you need to step out of your reality for a second.

I love this movie because of how raw Cagney played Tom Powers and how this film seemed to shape so many others that would follow suit.

You know you've made a classic when dialog from your film is quoted on a daily basis. Released in 1983, directed by Brian De Palma, written by Oliver Stone and staring Al Pacino, Scarface really can't go wrong.

This is a graphic and gritty depiction of the drug trade in 1980s Maimi. Tony Montana is a Cuban immigrant who rises to the top of the cocaine trade. A modern day rags to riches story, Tony shows us that like all things, what goes up must come down and Tony goes down in a blaze of glory reciting a line that will put Scarface into cinema infamy.

An interesting piece of trivia coming from IMDB says the De Niro was originally offer the role and while I can't imaging anyone but Al Pacino in this role, it would have been funny to see De Niro go, "You talkin to me, mang?"

"What do hear, what do you say?"

Angels With Dirty faces came out in 1938 and stars James Cagney, Humphrey Bogart, Pat O'Brien and Ann Sheridan.

Cagney plays Rocky Sullivan who grew up in Hells Kitchen with his best buddy Jerry Connolly. Jerry grows up to be a priest and Rocky grows up to be a gangster. Jerry works hard to keep the neighborhood kids on the straight and narrow yet Rocky's smooth talk and fast money is too much for these "Dead End" kids to resist.

This film leaves us decide on the virtue of Rocky's final moments but Angels with Dirty faces is another classic gangster film that will surely keep your attention the whole way through.

This movie also shows why Cagney was one of the greatest.

Brian De Palma does it again with De Niro, Connery and Costner.

With David Mamet behind the pen, the story of Elliot Ness verses Al Capone has never been told better.

This is also one of those movies where the music and sound is almost a character in itself. Composed by Ennio Morricone, the soundtrack surrounds you and pulls you into Chicago gangland.

De Niro and Connery steals the screen every time they're on. Connery gets a Supporting Actor Oscar for his work while De Niro gets to drop his bodyfat down to 3% for Cape Fear.  Somehow seems like a raw deal.

Released in 1987, The Untouchables is filled with great lines, great drama and great performances.

Starting with this film, the list now gets personal. A Bronx Tale is a coming of age film first, then it's a gangster film.

Written by Chazz Palminteri based on his one man show on broadway, A Bronx Tale was also Robert De Niro's directorial debut.

Released in 1993, A Bronx Tale came at a time, where for me, like I'm sure for many other young men, I really needed this film. There are so many wonderful lessons that are woven into the humorous and sometimes tragic events. Calogero "C" grows up in the 60's, a tumultuous time in America and is befriended by the local mob boss. "C" then has to weigh the lessons of his father with the lessons of his friend, Sonny the wiseguy, and then, while coming into his own manhood, decide how to live.

The dialog here is second to none.  Chazz Palminteri plays the boss Sunny so naturally and De Niro directs the whole film in a fluid reality of comedy and tragedy. If you haven't seen this, don't rent it, just buy it, because seeing it once will never be enough.

Where does one start with a movie like this? What an outstanding cast and script based on the real life story of FBI Agent Joseph Pistone.

Released in 1997, staring Johnny Depp and Al Pacino, Donny Brasco gives us an inside look at life in the mafia circa 1970s. Depp plays Pistone and we watch him infiltrate, under the guise of Donny Brasco, right into a mafia crew. He uses his developing friendship with Pacino's character, Lefty, to gain the trust of this rising faction of the mob.

Pistone/Brasco eventually faces an inevitable moral dilemma that climaxes the film while Pistone wrestles with keeping his family together as well as his soul. Depp does a great job with this role.

Pacino takes us to school in character acting in Donny Brasco and any student or aficionado of the craft of acting should watch this film with a pen and paper. Take notes kiddy's this is how it's done. I'm still trying to figure out how this performance slipped past the Academy Award people....

Another true story come to life, brilliantly directed by Martin Scorsese. 

Released in 1990, Goodfellas tell the tale of Henry Hill who for as far back as he could remember, he always wanted to be a gangster.

How do you not fall madly in love with this movie?  De Niro, Pesci, Liotta.  To quote Donny Brasco, "forgetaboutit!"

Powerful performances backed by one of the best soundtracks to boot, Goodfellas, like so many other gangster films shows the ups and the downs of a life of crime.  These downs though are big.  Very big.  Liotta plays Hills and we see him go from young kid wanna be to full blown gangster.

Classic Scorsese direction and wonderful dialog, Goodfellas is a must for any decent gangster movie collection.

Do I even need to write anything down here? Is this not the best gangster movie of all time? Is it not a classic and epic tale of family? No wonder it won best picture? It was!

If you haven't seen this movie, the only question I have for you is, "how was it living under that rock for so long?"

Released in 1972 and based on the book written by Mario Puzo, The Godfather was expertly directed by Francis Ford Coppola and stars Marlon Brando, Al Pacino, James Caan and Robert Duvall, just to name a few. An all star cast that I would also like to nickname "the poor man's acting school." Simply by watching and observing how the entire cast listens and responds is a lesson on what good quality acting is as well as a testament to Sanford Meisner who coined the phrase, "acting is living truthfully under imaginary circumstances."

Watch, learn and enjoy!

Honorable mentions go out to the following:

• The Cotton Club
• The Roaring 20's
• American Gangster
• Miller's Crossing
• Once Upon a Time in America
• White Heat
• Bonnie and Clyde

Picking faves is always a challenge, especially when you're talking a good gangster flick. Keep the conversation going though below. What are your favorite gangster films and how have they played a part in your life?