I didn't begin watching The Wire until I began renting the DVDs through Netflix, probably while season four or five was on the air in real time. I watched dutifully in order.
What struck me, and what I thoroughly enjoyed, were the comparisons of institutions. Each had its hierarchy, and each seemed to operate in a similar fashion but for the product. All pawns, whether officers or reporters or drug dealers, seemed captured in the same cycle of fruitless behavior. Swimming upstream wears you out. A crusade is often futile.
Of the five seasons, I would rank them as follows, from best to worst: 4 (schools), 2 (docks), 3 (police/politics), 1 (drug dealers/wiretap), 5 (newspaper).
As a journalist, I connected immediately with the newspaper angle of season five, the pressure to "do more with less" even though less, by its strict definition, is less. One can only do less with less. I loved the stevedores chapter of season two, particularly showing the huge gap between the police and the real supplier of narcotics and other illegal goods. And as the dock union president astutely noted, "now we just put our hand in the next guy's pocket." The kids in season four hit home because we write about it weekly. For every Dukie someone tries to help, there's dozens more like him coming up through the system. Each season builds on the last. Watch them in order. It's like an American novel.