1. Little Miss Sunshine
The weird thing is, I've only seen this movie once. I was having a really rough patch at one of my jobs in South Korea, and one of my friends had me over for drinks and noraebang duets and watching this movie. "It's the perfect movie to watch when you feel like shit," she told me, and it is. It gave me the renewed determination I needed to leave a toxic job—and wouldn't you know it but I found another job just a week after I gave my 30 days' notice, the best school I worked out in Korea hands-down.
I haven't really felt that worn-down and stressful since, but I know that if I ever do, this will be an instant pick-me-up. Do what you love and fuck the rest.
2. My Neighbor Totoro
This movie is just pure feel-good, 100%. There might be some darker shit going on behind it, but I steadfastly choose to believe otherwise.
3. The Comedy of Terrors
I stumbled across this one at my favorite Suncoast Video back in high school, one of MGM's "Midnite Movies" series of double billings. This one came on a disc with The Raven, a horror-comedy adaptation of Poe's poem of the same name by none other than Roger Corman. It's fun and goofy but it doesn't stand up to The Comedy of Terrors, even though both were written by Hollywood legend Richard Matheson.
I loved it from the first and I love re-watching it. My favorite is to watch it with someone who hasn't seen it before, because whatever they're expecting, this movie subverts it. A childhood of watching Mystery Science Theater 3000 may have made me an unlikely expert on low-budget horror movies of the 50s and 60s, but it wasn't until I saw The Comedy of Terrors that I truly began to appreciate the wonderful camp that is horror movie staple Vincent Price.
4. Pitch Perfect
The movie is hilarious, but I have to admit that my "comfort" part is the last performance at championships (or nationals or regionals or whatever they're called). I am a sucker for OTT music performances as a Crowning Moment of Awesome. I have watched that clip on YouTube too many times to count.
Honorable mention for this slot includes the battle of the bands scene in School of Rock and the final concert by Mr. Holland's grown students in Mr. Holland's Opus.
5. The Goonies
A childhood classic. I never saw it in the theaters (I was born too late for that) but I watched it a lot on tape. My brother and I had a babysitter (not quite like a nanny—it was more like a daycare thing, only we were the only children she watched, and she took care of us right in her home) and her son, maybe like five or six years older than me, was our big brother and hero. He taped loads and loads of movies from TV and then watch them with us. The Goonies was one that got a lot of repeat viewings. It's not a perfect movie—even 6-year-old-me was irritated by the girls' irritating and useless characters, sensing an injustice I couldn't quite put to words at the time—but I love it and never tire of it.