Deck the Halls: Matthew Broderick used to make some fun movies, but this wasn't one of them. Instead, it's an over-the-top holiday battle between neighbors so annoying that in the end you don't care who wins. In fact, if you sat through the whole thing, you're the one who lost.
For: The neighbors who are always getting on your last nerve, from trying to get you to buy stuff for their kids' fundraisers to constantly showing off their new cars.

It's a Wonderful Life: It's Capra, it's James Stewart, it's classic. It's also surprisingly dark for a good portion of the story, dealing with themes of despair, sacrifice, and even suicide.
For: The artsy friends of yours who think TV is just so plebian and thus haven't seen this movie one of the five hundred thousand times it's been broadcast. Seriously, though, why are you friends with them?

Santa Claus Conquers the Martians: You spent more money making Christmas stockings out of felt and glue and old buttons than these people spent on making this movie. This 1964 below-Z-grade flick became a favorite (or "favorite") on Mystery Science Theater 3000. See the original before someone remakes it, like producer David Zucker was threatening to do for a while.
Primarily For: MST3K fans.
Also For: Anyone who just thinks the Martians have it coming.

The Santa Clause 3: The Escape Clause: Look, the first movie was kind of cute. The second movie wasn't horrible. But this thing... this thing will suck the holiday spirit out of even the peppiest of Christmas elves. This was a case of a decent idea getting run into the ground like a hapless reindeer under the wheels of a Sherman tank for the sake of squeezing a franchise for all it was worth.
For: The scientists in your life who are on the verge of discovering time travel, so they can go back in time and convince Tim Allen to give it up before it's too late.

Surviving Christmas: Ben Affleck plays a wealthy jerk who pays a family to pretend to be his idealized kin over the holidays. There's the requisite "touching" turn-around that all rich A-holes in Christmas movies experience, but chances are you'll want to jab Affleck's character with pointy candy canes anyway.
Primarily For: Ben Affleck fans.
Sarcastically For: Your coworker, who you kind of hate, but you drew her name for Secret Santa. First, make sure she is not a Ben Affleck fan.

A Christmas Carol: There are many, many movie versions of the Charles Dickens classic. Stick with the 1938 version, or the 1951 version called Scrooge. Take your pick; they each accomplish the same thing as far as gift-giving goes.
For: Your boss, after making you work through Christmas Eve.
Follow-up Gift: Show up outside the boss's bedroom window later that night to rattle some chains.

Black Christmas: Make sure to get the 1974 version starring a young Margot Kidder, which is nowout on BluRay. Unless you hate the recipient, in which case feel free to give them the 2006 version starring Michelle Trachtenberg.
Primarly For: That slightly creepy friend who thinks it must be cool to be Santa because then you'd get to sneak into people's houses.
Also For: Anyone who needs the crap scared out of them after choking down a bowel-blocking portion of extra dry cornbread stuffing.

Which holiday movie would you recommend for someone you dislike?