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I forgot that I used to fall asleep to G4's Cinematech (I think that was the name of the program.) It was almost a proto-let's play channel. It would have cutscenes, trailers, and gameplay of lots of different types of video games from across all generations. There was no host, or anything. It would just cut from video game to video game.
For me it hast to be GamesMaster from the early 90's, it was one of my earliest experiences with gaming where they would have a few game challenges and a Q&A section with Sir Patrick Moore and reviews of old games (which were new when originally played) it reminds me of a much simpler time. Plus, I find new enjoyment these days looking back on all the sexual innuendo the host came up with.
I keep running into clips of Simpsons of old in my recommended YouTube feed and it keeps reminding me of how incredibly good this series used to be, and how some of its jokes aged way too well. I need to watch some of the full old seasons sometimes. Good times.
Rymoka's youtube channel has a lot of those old toonami promos, they're all great. Melancholic nostalgia for when you're lying in bed awake at 3am wondering where your left turned left.
As for me, I don't have any particular comfort movies, but I do rewatch old anime from time to time when I'm feeling down. Kenshin, Cowboy Bebop, Trigun, FMA, Outlaw Star, Champloo. Whatever matches my mood. Or I'll replay old video games for comfort. Maybe speedrun SotN for the 1000th time, or replay the entirety of Wild Arms or LUNAR. Maybe hop on to ol' Destiny 1 and do some 10-minute strikes, Dragon's Dogma to take down the online dragon with Maker's arrows, or emulate River City Ransom (or the RCR-inspired PS3/360 Scott Pilgrim game) to beat up on some fools. Maybe Warframe.
The problem I seem to have is that there are too many options that are close to comfort but not really comfort. It always feels like there's something better I could be doing/watching/playing.
My dad was a big kid, and we spent a lot of time watching Disney cartoons together. Or Hannah Barbara. So if I wanted to get really nostalgic I could put on Gummi Bears or The Smurfs or something, and I do miss the feeling of creativity old cartoons used to inspire. There's something about 80s cartoons that's hard to capture these days. The Last Airbender and Samurai Champloo do a good job. But as for things like that, I do still adore Toonami age anime, and will forever treasure Bennet the Sage for revisiting pretty much everything from that era in Anime Abandon, and have found quite a few quality recommendations. It's always fun to find something new and nostalgic at the same time