Original air date: 12/1/1999
Mr. Hankey hosts a Christmas Musical Episode, featuring South Park characters singing warped renditions of classic Christmas songs.
- "Mr. Hankey, the Christmas Poo" – Postman and Company
- "Dreidel, Dreidel, Dreidel" – Kyle, Cartman, Stan, Sheila and Gerald
- "O Tannenbaum" – Adolf Hitler
- "Christmas Time in Hell" – Satan and Residents of Hell
- "Carol of the Bells" – Mr. Mackey
- "O Holy Night" – Cartman
- "Merry Fucking Christmas" – Mr. Garrison
- "I Saw Three Ships" – Shelly
- "Medley: Joy to the World/Up on the Rooftop/Away in a Manger/O Come All Ye Faithful/Hark! The Herald Angels Sing/Silent Night/Rio/Let It Snow" – Jesus and Santa
- "Have Yourself a Merry Little Christmas" – Mr. Hankey, Kyle, Stan, Cartman, Kenny and Company
"Mr. Hankey's Christmas Classics" contains the following examples:
- Bowdlerise: In the album version of "The Dreidel Song", Cartman sings that "dreidel's fuckin' gay". In the episode, it's changed to "dreidel's friggin' gay" despite the many uses of "fuck" elsewhere in the episode.
- Brick Joke: Stan and Kyle decorate a chandelier with garlands and balls. It later snaps due to the weight and lands on Kenny.
- Cluster F-Bomb: Mr. Garrison's song "Merry Fucking Christmas".
- Did I Say That Out Loud: While the boys and Sheila sing about the Dreidel.Gerald: Courteney Cox, I love you/You're so hot/on that show...
- Falling Chandelier of Doom: Kenny falls victim to one during the finale.
- It's All About Me: Cartman's rendition of "O Holy Night" is largely about him being thankful for Jesus' birth because it means he (Cartman) gets presents for Christmas. He even takes the Wise Men's gifts to the Savior!
- Go-Karting with Bowser: Satan and Hitler show up on the surface at the end, not to take over the world, but to sing "Have Yourself a Merry Little Christmas" with the rest of the cast.
- Green-Eyed Monster: When Santa and Jesus team up for a medley of songs about themselves, the former gets upset because Christ has many more numbers in his repertoire, forcing jolly old St. Nick to sing Duran Duran's "Rio" just to get a few notes in edgewise. Jesus, being the ultimate Nice Guy, apologizes and coaxes Santa into a final duet of "Let It Snow" to cheer him up.
- Musical Episode: The episode features ten vignettes where the South Park characters perform holiday songs.
- Pet the Dog: Cartman sings along with the rest of the cast with genuine feeling, kindly sees Mr. Hankey off, and literally pets his own cat during the "Have Yourself a Merry Little Christmas" number.
- Shout-Out:
- The "fighting the frizzies
" newscast gag is a reference to a similar clip that can be seen on bootlegs of The Star Wars Holiday Special. - The opening song is sung by a postman that resembles Postman S.D. from Santa Claus Is Comin' to Town.
- The end of "Christmas Time in Hell" features a caricature of James Stewart and his famous It's a Wonderful Life line "Merry Christmas, movie house!"
- The duet is a reference to the 1987 Dustin Hoffman/Warren Beatty spy comedy film Ishtar.
- The "fighting the frizzies
- Stylistic Suck: Some of the musical numbers are traditional Christmas songs sung badly. Cartman flubs a lot of his lines in "O Holy Night," and Mr. Mackey's rendition of "Carol of the Bells" is pretty flat, his voice carries no weight, and he can't stop attaching his "M'kays" to the lyrics.
- Super-Strength: Shelly shows off a feat of this when, fed up with Stan and Kyle making faces behind her back during her performance of "I Saw Three Ships", easily lifts the piano and drops it on them.
- Take a Third Option: Jesus and Santa use their medley to sing songs about their own lives (replacing their names with first-person pronouns), but Santa feels left out because there are so many more songs about the Savior than him. Jesus realizes the mistake and instead starts singing "Let It Snow", a song which doesn't mention either of the two. This placates Santa enough to join in.
- Take That!: Hell eagerly awaits the death of Andy Dick.
- They Killed Kenny Again: A chandelier falls down and crushes Kenny during the last musical number.
- Villains Out Shopping: "Christmas Time In Hell" has Satan throwing his own Christmas celebration in Hell, with all the damned and demons singing, dancing, laying cookies out for Santa Claus, stringing up Christmas tree, and literally shopping for gifts.
