Airdate: Monday, December 18, 2006

Homestar and pals star in a second series of short shorts, this set holiday-themed, in which Strong Bad writes a letter to a Decemberween present he is certain of receiving, the Homestar characters are depicted as ornaments on a Decemberween tree, an Old-Timey short shows Homestar giving a Decemberween present to Rumble Red, Strong Sad writes a letter to Decemberween present he is certain of receiving, and Homestar sings a song to Coach Z about how to behave so he won't be alone on Decemberween.

Tropes

• Clothes for Christmas Cringe: Played with in the first short. Strong Bad writes a letter to "tube socks" claiming the socks will hear some hurtful things from him, cutting to a montage of his disappointment in getting them as gifts. He states that the socks shouldn't believe a word of it; he loves the socks but he has an image to keep up. A later short has Strong Sad starting to write a letter to "argyle socks".
• Collector of the Strange: When Homestar advises Coach Z not to talk about his "embarrassing physical problems", Coach Z responds "I collect those!"
• Continuity Nod: Several, especially to Decemberween toons of the past:
  • This is a sequel of sorts to "Summer Short Shorts".
  • In the Decemberween tree short, two references are made to the Strong Bad Email "what I want". The Coach Z ornament is the commemorative ornament that appeared in that email, while Strong Bad is depicted as a homemade ornament made out of Styrofoam and plastic sequins. In "what I want", Strong Bad denounced homemade ornaments as "anti-gifts".
  • In the Homestar and Coach Z short, Coach Z gets drunk on Listerine, as in "The Best Decemberween Ever".
• Damned by Faint Praise: Homestar Runner tells Coach Z that if he pronounces his words correctly he'd find that people might not throw up so much when they talk to him.
• Elmuh Fudd Syndwome: During his song to Coach Z, Homestar advises him to "say words right", but due to his own speech impediment, it sounds like "say wouds wide", which, in fact, is what he writes on a blackboard.
• HA HA HA—No: Homestar displays this when Coach Z asks him if he may come to Homestar's house for Decemberween.
  Homestar: No, no-ho-ho! No, no, no. No, Coach Z, no. No. (suddenly angry) No, you can't.
• My New Gift Is Lame: Strong Bad actually likes getting tube socks as a Decemberween present, but pretends to hate them just to keep up appearances. He even writes a letter to his future present, to apologize in advance.
• Noodle Incident: Why does Strong Bad not want people to think he has a soft spot for tube socks? Because "it took me years to live down that Martina Navratilova poster, and I will not go down that road again."
• Offscreen Teleportation: Right after Coach Z says he's got a lot of parties and isn't a loser, the camera zooms in on Homestar and one second later Coach Z is somehow already hung over and upside-down in a locker.
• Off with His Head!: Ultimately, the gift to Rumble Red kills him by releasing a bear trap that closes over his neck and beheads him.
• Porn Stache: The ornament version of Coach Z dates from 1974 and features the coach with a bushy mustache and huge afro.
  Coach Z: The '74s was the prime of my dating year! In those days, ladies would go out with anything that had a mustache.
• Rube Goldberg Device: Old-Timey Marzipan's gift to Rumble Red is a bundle of dynamite... which opens to reveal a pistol... out of which comes a cement mixer... which drops a bear trap on Rumble Red.
• Strange Minds Think Alike: One short begins with Strong Bad writing a letter to tube socks. Another features Strong Sad writing a similar letter to argyle dress socks.