Mad Men uniquely holds up after almost two decades
Rewatching the series this last month has left me astonished at how actually great this show is. I loved it on my first watch 10 years ago, but I was too young to appreciate the incredible craftsmanship and story telling.
There are so many details about characters, events, plot, and culture that are shown only implicitly or as foreshadowing for the future. Yet even if a viewer doesn't catch all of that, the show isn't diminished. The acting and dialogue is so good that reading between the lines isn't necessary at all. Achieving that, where one viewer is happy on the surface and another can choose to (or not) dive in is what I think really defines great art.
Other prestige TV shows got by with hype (Game of Thrones), surprise (Silo), or cultural commentary (Severance) but get weaker after the first time through. Mad Men doesn't. It is stronger after rewatching it.
What a great show
Edit: to add an example, S6EP02 has two great moments back to back. Minor spoiler>!Roger getting a shoeshine box from a man who died right as Roger is realizing he is alone in the world and begins crying (a great performance by John Slattery there) then Megan and Don showing slides on the Kodak carousel of their trip to Hawaii. We last saw the carousel when Don was sleeping around while married to Betty. He became teary eyed at the reminder of how much he cares about his life and knowing he's making mistakes. This time, with Megan, Don is flat, no emotions, no remorse or regret. The parallel and meaning is great.!<