I love The Office (US) and Black Mirror. I don't rewatch/reread many things, but I could honestly watch Black Mirror once a year and not get sick of it. I love The Office because it's just... a love story/tribute to the average American midwestern life, in a way. It also reminds me of happier times as a teen when I'd watch it and then go to school and talk about it with my fave teachers, and come on SS and talk about it with Kelvin. I think we both watched all of it one summer, maybe around when S3 or S4 or S5 was airing/had just aired...? I'll have to Google what year that was. (09)? Ok after some Googling, the date was right, had to be 09, but I cannot keep track of the seasons of that show. GUESS I'M DUE FOR A REWATCH.
My favorite film is, and may ALWAYS be, The Dark Knight.

So many reasons here, but it has such a tight plot/iconic dialogue/excellent cinematography/complex meaning/commentary/I could go OFF.
Anything with a lot of interior meaning and layers of complexity gets me.