Probably the only one given the film's dark nature. It always gets a chuckle when Rose is first attacked in the "Dark World" of Silent Hill by the gray children and passes out, only for her to wake up in a brightly lit bowling alley with Johnny Cash's "Ring of Fire" playing in the background. Of course, even this moment of humor becomes Harsher in Hindsight when you realize whyRing of Fire is playing.
As Thomas and Chris drive through Silent Hill, Thomas keeps saying over a microphone that he will take Rose to safety. Chris asks him why can’t he do that [talk on the microphone]. Thomas responds with saying that 90% of the time, when a wife takes a run and takes the daughter to a place like this (Silent Hill), “I’d say she’s damn mad at her husband.” Chris gives a clear disapproving look at him.
The sequel features a bizarre jump-scare with a Pop Tart. Whether that sort of borderline self parody is appropriate for a film dealing with such dark themes is a part of why this movie is such a base breaker, but it's still pretty funny.
Bloody Hilarious, but the scene in the sequel where Sharon looks in the back kitchen of the Happy Burger, and sees a Cannibal Larder where a deranged-looking butcher is slicing off pieces of flesh made from living people hanging from meat hooks, and then there's also a fairly normal-looking skinny cook who is just casually flipping the resulting burgers like it's all part of his normal job routine. The only thing that's missing from the scene is the cook smoking a cigarette.
On a meta level Sean Bean, whose character dies in game, somehow survives BOTH movies, promptly launching said character into the realms of Memetic Badass.
Silent Hill Ascension
The Berry Man. One of the "perks" of paying real money in order to help choose what will happen is a chance to have your avatar cameo in the story. This has led to a bizarre scene where Crimsonrain 722 as The Forager appears in the woods, says that he's foraging for wild berries, mentions seeing strange things without any elaboration, and then says he likes making jam and selling it in town (in Silent Hill?) before just leaving, having contributed nothing.
. One of the "perks" of paying real money in order to help choose what will happen is a chance to have your avatar cameo in the story. This has led to a bizarre scene where Crimsonrain 722 as The Forager appears in the woods, says that he's foraging for wild berries, mentions seeing strange things without any elaboration, and then says he likes making jam and selling it in town (in Silent Hill?) before just leaving, having contributed nothing.