Elf
(2003)
Will Ferrell is one of those actors that you either love or hate. Even if you don't like Will Ferrell, however, you might still enjoy Elf. My wife didn't like Will Ferrell until she watched (and subsequently loved) Elf.
Elf is the story of Buddy, a human who, after crawling into Santa's sack in an orphanage, is raised by Papa Elf in the ways and tradition of the elves. When Buddy is in his thirties, he finally figures out that he is not an Elf. He is told who his father is, where he lives, and that he is on the Naughty List. Buddy goes on an adventure to New York to find his father, and he might save Christmas along the way as well.
Buddy is an overly cheerful person who is the single most naive person in NYC. He eats the gum stuck to the railing by the subway entrances. He gladly takes fliers for anything from the annoying people on the sidewalk. He has no knowledge of the real world. This is, of course, where all of the humor comes from. And it is always funny watching Will Ferrell getting hit by a taxi cab.
One of Buddy's favorite things to do is sing. That is because "the best way to spread Christmas cheer is singing loud for all to hear". He sings a bunch of impromptu songs throughout the movie, like the song about being in a store and singing, or the great little tune he makes up for his dad when they first meet.
If you haven't watched this because of how you feel about Will Ferrell, I beg you to give it a chance. There's also Zooey Deschanel in this one, so that should help, right?