One of my fave holiday songs is also one of the most controversial—"Baby, It's Cold Outside" by Frank Loesser. First featured in the 1949 movie Neptune's Daughter, it tells the story of a Romeo trying to convince his coy gal to stay the night by reminding her of the heavy snow, the biting winds, and how her eyes look like starlight. It's very flirty, cute, and by some accounts, rapey. The line most people have a problem with is when the gal sings, "Say... what's in this drink?" and of course the first thing that pops to mind is ROOOOOFIEEEEES!! However, don't forget this song was written in 1944 and the reference is most likely as innocent as spiking the punch.
STILL, it's hard to find anyone to sing this song with me in karaoke because of the controversy—though Zooey Deschanel and M. Ward of She & Him skirt around the issue in their new video of the song, by reversing the roles. THIS IS NOT THE BEST VERSION OF THIS SONG YOU WILL EVER HEAR (rather this is), and I'm pretty annoyed by the "apologist" bent. However, the animation is cute, references Stephen King's Misery, and then goes back to being cute again. Check it out.
Oh, and here's the original version featuring writer Frank Loesser and his wife Lynn. They used to perform this at Hollywood cocktail parties which makes me deeply regret not being born into that time and life.