There seems to be a right time for watching fun movies... For me it's:
Reservoir Dogs: Best time to watch: Summer/Fall: Friday afternoon, just as the sun is setting, 5:30-6 pm.
Repo Man: Best time to watch: Summer, 12-1 am Great late-night movie.
The Thing: Best time: Winter (with Snowfall): Sunset, 5 pm.
Barfly: Best time: Spring/Summer, 8 pm. Preferably after eating a cold-cut hero and after many beers.
Factotum: Best time: Spring/Summer, 6 pm. After this, after the sun sets, you'll want to move on to Barfly.
Faster Pussycat, Kill! Kill! : Best time: Anytime of year, 11am-12pm - afternoon delight.
Pulp Fiction: Best time: Spring/Summer: Dinnertime, 6 pm.
True Romance: Best time to watch: Winter, 8 pm.
Scarface: Best time to watch: Hot summer night, 11 pm.
Death Proof/Planet Terror: Best time to watch: Summer, Weekends, 5 pm. It should get dark outside as it gets dark outside in Death Proof, then proceed to Planet Terror.
The Fog: Best time to watch: Fall, 10 pm. Very isolating movie, great for the malaise that comes with Fall.
Incredibly Strange Creatures: Best time: Summer, 1 am.
Evil Dead: Best time: Summer/Fall, 2 pm. Scary in the daytime--I think because it's daytime for a long while in the film.
Phantasm: Best time: Summer/Fall, Begin at 4 pm. Another scary, daylight-filled movie. Oh, and then you MUST proceed to Phantasm II.
Basket Case: Best time: Summer, afternoon movie, 4 pm.
Hellraiser: Best time: Anytime of year, 4-5 pm. If it ends AS the sun sets, it'll scare you even more.
Plan 9 From Outer Space: Best time: Anytime of year, 10 am. You won't feel like you've wasted your whole day when it's over at 11:30.
The Cabinet Of Dr. Caligari: Best time: Anytime of year, 1 am. Best when your mind is limber.
Pee Wee's Big Adventure: Best time: Anythime of year, 10-11 pm. You want to be giddy after midnight rolls around. Great late night movie.
After Hours: Best time: Anythime of year, but Summer/Fall is best. Begin at midnight--DUH.
Xmen: Best time: Winter, Dinnertime--6-7 pm. Only one part per evening.
Body Double: Best time: Summer, 6 pm. Again, creepy if you watch this as it gets dark outside.
Playtime: Best time: Anytime of year, Summer is best. 4-6 am. Trust me on this.
Naked: Best time: Fall/Winter, 7-8 pm. You'll want more time to watch something else afterwards.
Bad Lieutenant: Best time: Anytime of year, 3 pm. You'll want A LOT of time to wash this one off your brain.
Amelie: Best time: Christmas or New Year's. 6 pm.
Ed Wood: Best time: Anytime of year, 10 pm.
The Thin Man: Best time: Christmas Eve or New Year's Eve, 8 or 9 pm. Or, if you want to do the whole series, try watching from Christmas to New Year's. Drink heavily too.
Buffy, Seasons 1-3: Best time to watch: Begin when school begins, September. Finish in Winter.
Begotten: Best time to watch: NEVER!!! Don't ever watch this movie! It was beautiful when I saw it, but then it proceeded to haunt my memories and mysteriously depressed me deeply for over 30 days afterwards!