The Sopranos (1999)

I'm late to this, I know, but at the time it came out I was in college and working multiple jobs to pay for it. It came out in that stretch of time that I was practically blind to current culture. But now I'm watching it, and honestly it's like all those other Mafia movies and TV shows that come around every decade or so. They never really get old. The Mafia allows for a few things, stress, tension which are both great for drama...and then brutal violence and humor, which also pair wonderfully together. The only time you're going to miss is when you don't do it well, but The Sopranos actually did it incredibly well. It was amazingly fun, amazingly dramatic, and beautifully acted...so, it's going to entertain. And, unlike the movies, the episodic nature of a TV show plays well with the mafia shtick, especially when paired with a premium channel like HBO that can do whatever they want.