From the song "Do you Hear What I Hear?"
Hey song, do you know what I know? I know that if a newborn baby is shivering in the cold, the thing to bring him is a blanket or heat source, not METAL. Then again, this song opens with the wind talking to a lamb, so dumping freezing coins on an infant might actually make sense here.
From the song "Have a Holly Jolly Christmas"
Have fun explaining to your girlfriend why you're making out with her on behalf of Burl Ives. It doesn't help that he sounds super drunk in the song.
From the song "Chipmunk Song (Christmas Don't Be Late)"
We're dealing with anthropomorphic singing chipmunks here, but still. Dave, their wrangler/manager/father(?) should tell them that because Christmas occurs on December 25th every year, it can never arrive late, but he's too busy screaming at them for not hitting the notes in this weird song. Merry Christmas!
From the song "I Saw Mommy Kissing Santa Claus"
The central conceit of this is that the kid doesn't know that it's his dad in the Santa Claus costume, so he thinks his mom is kissing Santa, while his dad is nowhere to be found. So I guess if you think being scarred emotionally by your childhood fantasies is funny, then, yeah, this scenario would be a real "laugh".
From the song "Santa Claus is Coming to Town"
Why are we afraid of the NSA when this creep is watching children sleep 24/7? Wait a minute. Think about it. The NSA was exposed by Edward SNOWden? It all fits! It all makes sense! Of course [THE REST OF THIS ENTRY HAS BEEN REDACTED.]