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January was the first month of 2020. Not a lot happened this month. No new videos or even photos of Chris's face were released. However, he did bitch about his banning from The End Games and gained an interest for Dungeons and Dragons.
- 1 January - New Year's Day arrives; Chris welcomes in the Twenties with one of his classic songs.
- 4 January - Chris gets a "healing" crystal-infused water bottle as a gift.
- 15 January - After failing to pay server fees and their sysop's arrest, Encyclopedia Dramatica shuts down.
- 17 January - On Twitter, Chris insists he be unbanned from The End Games to learn how to play Dungeons and Dragons for him to complete the Dimensional Merge.
- 23 January - The End Games reaffirms that Chris is not welcome in their shop by blocking his Twitter account, to which Chris whines that they are not inclusive and that their reputation has been sullied by banning him.
- 25 January - The 11th anniversary of the CWCki's founding.
- 26 January - An anonymous envelope containing a drawing of a creepy stare arrives in The End Games's mailbox. They upload it to Twitter.
- 29 January - Ben Saint returns after months of quiet to Chris's attention on Twitter; he and Chris together solicited crowdfunding for a convention.
- 30 January - Two creditors sue Chris for debt, bringing the Chandlers' running count of debt cases received to eleven. 
- 30 January - Chris unveils his in-progress Dungeons and Dragons character sheet, then passive-aggressively uses the Creamarina Twitter account to comment to The End Games, who had blocked his main account, about it.