The two biggest fictional things I’ve gotten truly obsessed with are Stephen King’s The Dark Tower series and Twin Peaks. Something about those two things - the contining enigmas, the unexplained and inexplicable plot points, and so on causes their fanbase to get batshit insane about them. I like this.
What else out there is like this - obsession-causing and worth it?
Tolkien!
Sounds like you’d love Carnivale.
Season 1 is on DVD, and Season 2 is playing on HBO right now. I’m pretty pathetically hooked.
For insanely detailed dissection of everything from eye color to background music, and what each portends, check out the forums at http://www.carnivale.org/
As a bonus, there is lots of symbolism involving towers, and the show stars Michael J. Anderson, from Twin Peaks.
Atlanta Nights by Travis Tea. 
The Marx Brothers, Monty Python, and the Diana Rigg-era Avengers.
Thanks for reminding me of this! I saw a promo on HBO at a friend’s house recently, and my jaw sort of dropped - “What is that?” I recognized Michael from Twin Peaks immediately, and the entire concept of the show sounds amazing. I’m adding it to my Netflix queue right now!