1. The Wire (2002–08)
You've heard this one before: The Wire is the best show HBO's ever made. During its five-season run, David Simon's Baltimore-set drama earned heaps of critical praise and cultural cache, but suffered, weirdly, from poor ratings and awards-season malaise. (It won zero Primetime Emmys.) It's easy to see why it's regarded as being so innovative and intricate. After the first season introduced viewers to the Avon Barksdale crew and the detectives tasked with investigating them, The Wire twists the anthology format to spotlight other corruption around the city, from the docks to City Hall, and tackle controversial ideas, like Season 3's drug-legalization plotline. Everything in The Wire is connected, and everyone is a little bit tainted, with politics, police, drugs, race, and crime intersecting through iconic characters like Avon, Stringer Bell, McNulty, Greggs, Bunny, Bunk, and, of course, Omar. The show's fourth season, largely concerning Baltimore's education system, masterfully demonstrates the futility of human intervention in the face of systemic failures. Even factoring in The Wire's subpar fifth season, the show always managed to challenge the viewer in a medium that rewards superficial entertainment. In the end, we have to say it (sorry): The king stay the king.