1. Tony Soprano from The Sopranos (1999-2007, HBO)
Played by: James Gandolfini
Is there anyone else more worthy of this top spot than Tony Soprano? The broad-shouldered, overweight leader of the most prominent mob family in the Garden State brought movie gangster personality to the small screen, but with a far deeper examination of the psyche of a boss than the world had seen before (not even Michael Corleone sat for therapy sessions). During the course of the series, viewers saw Tony grow in stature as he rose through the ranks of the crime family thanks to his brutal style and street smarts.
But it's Tony’s family struggles and his personal foibles that make him feel like a true-to-life human, rather than a stereotype. This helped this otherwise despicable human being connect with audiences instead of repulsing them. Similar to Michael Corleone, Tony Soprano is the man you root for, and even when he’s busy killing foes in vicious mob style, he’s still a sympathetic figure.
Think about it: This is a man who rose to prominence and power off a business built on the blood of others, yet he still made viewers love him. Now that’s gangster.