Modern Gangster Movie Collection Captures Shades of Gray … and Red

The morally ambiguous films of the late 1960s and early 1970s changed cinema as we know it. They also allowed modern gangster films to dig deeper into the murky souls of their antiheroes. 

Ultimate Gangster Collection: Contemporary, available now on Blu-ray, gathers five essential mobster movies with an array of questionable characters and actions.

Mean Streets (1973). The Untouchables (1987). Goodfellas (1990). Heat (1995). The Departed (2006).

It’s a rogues gallery of shady types, complicated heroes and law enforcers who bend the rules to get their men.

Mean Streets, director Martin Scorsese’s first foray into the criminal underworld, cast Harvey Keitel as a conflicted wiseguy working on the lowest rungs of the crime ladder. Poor Charlie grew up around casual violence and illegal behavior, and he clings to his Catholic faith while pondering how his career will be regarded by the Man Upstairs.

He repeatedly puts his fingers near open flames as the thought of eternal damnation rushes to mind. He knows his chosen life is wrong, but all he wants is to get his hands on a restaurant to call his own and create his own morally upright world within it. His shady connections may prevent that from happening, particularly his ties to a loose cannon (Robert De Niro as Johnny Boy) who could undermine Charlie’s livelihood–if not his life.

The Untouchables offers a relatively clean good versus evil tale by gangster standards, with De Niro’s Al Capone summoning all the illegality any movie can muster. Our heroes, led by Eliot Ness (Kevin Costner), are pure of heart but pragmatic as the bodies begin piling up.

It’s up to old sage Jimmy Malone (Sean Connery’s Oscar-winning performance) to explain the rules to Eliot Ness that will give the lawmen a chance at victory over organized crime.

You said you wanted to get Capone. Do you really wanna get him? You see what I’m saying is, what are you prepared to do?

“Anything within the law.”

“And then what are you prepared to do?

The moral shadings in Goodfellas allows audiences to root for rising mob star Henry Hill (Ray Liotta), a man who idolized gangsters for as long as he can remember, while waiting for the inevitable fall from grace. We know Hill’s lifestyle is wrong, but some of his co-horts are so unabashedly vile he emerges as the lesser of so many evils. Besides, the way Henry flexes his power is mesmerizing, like a Sinatra figure maneuvering through a nightclub, the clientele parting to give him space.

Henry’s mob journey involves drugs, double crosses and exhumed bodies, and by the time the third act approaches we know he’ll be lucky to come out of it all alive. When he does, he considers himself just a “schnook” without any of the power or fame of his former life.

In Heat, De Niro plays a career criminal we find hard to hate. Compare him to Vincent Hanna (Al Pacino), a veteran cop whose bluster makes even his crime solving chops feel undeserved. The two circle each other for much of the movie, one filled with so many familiar faces you’ll have to keep pausing the Blu-ray disk to catch them all. The two may be destined to swap bullets, but their more eventful confrontation occurs within the confines of a diner’s booth.

It’s a moment that not only brings two screen legends together for the first time (they worked separately in The Godfather: Part II) but draws a chalk outline around the fuzzy protagonist games at the heart of Heat. The pair bond over career frustrations and their damaged love lives, their humanity uniting them before their destinies take over.

The Departed, the film that finally earned Scorsese a Best Director Oscar, is alternately thrilling and ugly, an oh, so modern portrait of gangster games. It’s a tale of dueling undercover agents, love triangles and roles so robust only Jack Nicholson could make them complete. We watch two moles work their way into both sides of the law, our minds figuring out just how the good versus evil ledger will balance out in the end.

The tale’s waning moments catch us off guard, proving that the moral shadings we’ve come to anticipate can be overturned with the right director pulling the proper levers.

The gangster genre allows for the kind of morality tales not easily digested. It’s why so many films in the genre demand repeat, if not incessant, viewing. It’s hard to watch any of the aforementioned films once and properly process the messages being imparted.