Snoop Dogg (Feat. Daz Dillinger, Nate Dogg, Bad AZZ, Tray Dee) 'Santa Claus Goes Straight To The Ghetto'
This special cut from the Christmas On Death Row holiday compilation features a classic sample from Isaac Hayes' "Do Your Thing" and a lot of smooth-as-silk rapping from Snoop Dogg and his West Coast crew. While the chorus warns that Santa Claus shouldn't get too close to Snoop Dogg's hood ("you might get shot"), the holiday track rejoices in staying real. Quips Snoop Dogg, "Now on the first day of Christmas, my homeboy gave to me/ A sack of the krazy glue and told me to smoke it up slowly." Maybe don't play this around your conservative grandparents.
Loretta Lynn 'To Heck WIth Ole Santa Claus'
Country sweetheart Loretta Lynn surprised everyone when she recorded this bitter ode to Old Saint Nick. Resentful after last year's disappointing Christmas, Lynn describes how she'd like to wreak havoc on her evil ex with quips like, "When he goes dashin' through the snow I hope he falls." 'Tis the season to be hateful?
Randy Newman, 'Christmas In Cape Town'
Leave it to cultural provocateur Randy Newman to record a Christmas song that's actually about racial tensions in South Africa. This disturbing and spooky recording off 1983's Trouble In Paradise describes a racist South African wishing his city could go back to the way it was. Hardly a Christmas song, the groundbreaking track unpacks issues of Apartheid and is truly the bleakest holiday we've ever heard described.
De La Soul 'Millie Pulled A Pistol On Santa'
Another relentless Christmas song, De La Soul's epic "Millie Pulled A Pistol On Santa" tells a story about a young girl that is sexually assaulted by her father. No one will believe her, as father is so prominent in the community that he even volunteers to play Santa in the department store. The icy rap track ends with a grisly death, as the daughter gets revenge by shooting her father point blank in the middle of Macy's. Merry Christmas to all?
Various Artists, 'I Saw Mommy Kissing Santa Claus'
Let's face it: this song is insanely creepy. While a child ponders his mother's infidelity with Old Saint Nick, he describes the incident that he will later share with his father. Of all the versions, a young Michael Jackson (of the Jackson 5) really hammers the message home: what you don't know about your parents won't scar you for life.
James Brown 'Santa Claus Goes Straight To The Ghetto'
James Brown's attempt at social consciousness was never more misguided than on his classic holiday album James Brown's Funky Christmas. While he describes a gift-giving Santa with presents to spare in the ghetto, James Brown tells Saint Nick, "You know that I know what you will see/'Cause that was once me."
Weird 'Al Yankovic 'The Night Santa Went Crazy'
In this charming Christmas comedy song, Weird 'Al wonders what would happen if Saint Nick ended up in a no-fly zone. "The Night Santa Went Crazy" is a charming ode to holiday-related post-traumatic stress. As Santa guns down his own workshop and holds his elves hostage, it makes your family drama seem tame by comparison.
Various Artists, 'Grandma Got Run Over By A Reindeer'
It wouldn't be Christmas unless this novelty song written by Randy Brooks for husband and wife duo Elmo and Patsy Trigg Shrosphire was heard at least once. Telling the story of a grandma who gets so sauced on eggnog that she escapes into a snowstorm, she meets her eventual grisly end with a collision with Santa's sleigh. After Elmo and Patsy sadly divorced, he recorded it as a solo cut in 1992. In 2000, the song was even turned into an animated holiday movie and aired on the Cartoon Network.
The Kinks 'Father Christmas'
This devastatingly awesome 1977 cut by The Kinks is an earnest nod to a holiday class uprising in Britain. The song tells the story of a department store Santa who is beaten up by a gang of poor kids and ordered to give them money, instead of toys. It rocks hard with a smart message. But you shouldn't let your kids hear it.
Ali Lohan (Feat. Lindsay Lohan) 'Lohan Holiday'
In 2006, Ali Lohan (a.k.a. Lindsay's little sister) cut her own holiday album titled Lohan Holiday. While the album has several missteps, the title track is the most glaring. As Ali duets with her on a chorus that wishes you "a Lohan holiday, a winter wonderland that's oh so far away, don't have to go no where - just let your mind escape," visions of neglectful stage parents and prescription medicine dance in our heads. Poor Ali Lohan.