Bad Santa
Bad Santa might just be THE most anti-holiday of all the holiday movies (seriously, check out the trailer above). Billy Bob Thorton plays a mall Santa who just couldn’t give any fucks even if he tried (well, he gives literal fucks to the mom from the Gilmore Girls, but no figurative fucks). He essentially decides to work as a mall Santa one month a year so he can ultimately rob the malls and then disappear. It’s actually a pretty smart idea for a small scale way to pull of a heist, and if I didn’t think mall Santas were all fucking pedophiles, maybe I would try that some time.
What makes Bad Santa so great as far as holidays movies go is that you can feel its festering hatred for the holiday, and it doesn’t hold that back. It understands the stupidity of the zombie like masses who bring their kids to sit on a stranger’s lap and whisper their wishes once a year and does not refrain from pointing out how fucking stupid the whole holiday is.
It also manages to do that while being incredibly funny. Like a nihilist comedian.