Hitler's Pencil of Winter was Venkyra21's entry to JennieParker87's The "Merry Hitler" Contest. Originally uploaded on 17 December 2014 on his old channel Gokyr586, the video was later gone when that channel was taken down. A year after its original upload, the parody was later reuploaded again on his Vimeo channel on 19 December 2015 in the lead-up to its sequel parody, Hitler's Pencil of Winter Powers, which ended up winning the Parody of the Year award for the year 2015.
- Compared to its sequel parody, this parody received very little popularity when it was still on YouTube.
- This is one of the first parodies to use Gokyr586's final outro.