"Have Yourself a Merry Little Christmas"
While some object to this song because it is rather depressing, it is important to understand its context both within the film Meet Me In St. Louis and in American history. Within the movie, Judy Garland's character sings it to her younger sister to comfort her as they face leaving their family home in St. Louis. As you can tell by the clip above, this attempt isn't very successful. In regards to history, the song (and the movie) came out during World War II, which made the wistful tone more understandable and welcome. On another note, the song was supposed to be much more depressing than it was. For instance, it was supposed to contain the lyrics "Have yourself a merry little Christmas/ it could be your last/ Next year we may all be living in the past." Judy Garland argued against these lyrics, so the lyricist changed them to the ones we know today.
"What Are You Doing New Year's Eve?"
Although my coworkers and I used to laugh at this song because it sounded so despondent and desperate, it has grown on me over the years. Rather than being desperate, I suppose that the song seems a little more hopeful than I originally thought (even though the lyrics don't really suggest that the person's answer is going to be a positive one for the singer).
"My Dear Acquaintance"
I like the understatement of Regina Spektor's interpretation of this song. Although there is a debate (at least if one is to believe the YouTube comments for the song) regarding her use of irony and sarcasm in this performance, I am not entirely convinced that the song is necessarily that sarcastic (at least in the "Merry Christmas (the War is Over)" vein). While it does encourage reflection, I don't know if the tone is bitter enough to be considered sarcastic or ironic. Please forgive the rather odd clip - it was the only one with the entire song I could find on YouTube!