Let's take it back to '91, with De La Soul's sophomore album, De La Soul Is Dead, and specifically, the cut "Millie Pulled a Pistol on Santa". Those who know the song, understand this is far from your typical joyous holiday song. Faaaaar from it. Quite the opposite actually, and I chose it cause let's keep it real: shit is not all peachy and cheery for everyone during the holiday seasons, and we must not forget those who suffer.
And if that one's a little too dark for you to stomach, here's another Christmas-inspired song. OutKast's "Player's Ball". Specifically the original version from the LaFace Family Christmas album. The song was originally known as "Socks & Drawers". Source: Ego Trip's Book of Rap Lists.
OutKast - Player's Ball