The Big Lebowski if I'm forced to pick just one.

Not a movie, but every time I watch Willjum on YouTube smoke people in Rust it's somewhat calming for me.

I don't have a movie or tv show I watch over and over again. Always wonder why that is, as so many people seem to have such a thing.

Only ever had one, kinda. Though I'm not sure I'd call it comfortable? But it's... visceral, which is mildy amusing because it's trying to be cerebrial, but too much of the dialogue is just scattered quotes and philosophy references. Anyways, the movie is Ghost in the Shell: Innocence. The second one that was directed by Mamoru Oshii. These days, I don't get anything out of watching it anymore. I watched it one too many times. But I've never taken to any movie like I did that one, so, it wins.

Could watch a thousand times: Grease.

The Curse of the Golden Flower. I never get tired of watching it.

Not a movie, but mysteries at the museum puts me to sleep every time. They reuse the same overblown words for everything so it winds up that every single item they talk about sounds alike. Between that repetition and the guys metronomic cadence and almost whispery voice, puts me to sleep every time.