In October 2022, videos about Headless became increasingly popularized on TikTok (examples from 2022 shown below).

Posts about Headless become increasingly popular among the Roblox community every year leading up to and during October, including memes and videos about it.

On October 4th, 2020, YouTuber Slofix posted a video showcasing numerous costumes that are only available to owners of the Headless Head, garnering over 1.3 million views in two years (shown below). Since its release, players have been making unique costumes for their avatars that take advantage of this. The 'Headless Head' has become notably popular among Roblox players as the only item that makes the player's head invisible. On October 3rd, 2022, the Headless bundle was made available on Roblox for Halloween 2022. This is showcased in a TikTok video by posted on July 5th, 2022, garnering over 2.8 million views in three months (shown below). Rather than actually making the player's head invisible, the Headless Head is just very small and placed inside the player's torso. The Headless Head item has become one of the most desired and popular among players over the years with over 720,000 favorites as of October 2022. On October 10th, 2017, YouTuber Poke uploaded a video showing various ways to use Headless, including the SpongeBob skin, garnering over 650,000 views in five years (shown below). One of the most popular examples of this is a SpongeBob avatar, which requires the Headless Head to give SpongeBob the right shape.

Since the Headless Head item can be worn with any other non-head items in Roblox, players have found creative ways to make specific characters and costumes using it. 'Headless' has gone on special, out-of-season sales twice throughout the 2010s once in May 2013 for the Memorial Day 2015 sale and once around the same time for the Memorial Day 2016 sale. The Headless Head can be worn with any other Roblox clothing items and is not relegated to the headless horseman outfit. It is only available for purchase in October through November, often between the dates of October 1st or 3rd and November 1st or 6th. The bundle, which goes for 31,000 Robux (over $300 USD) includes seven items to make your avatar look like the headless horseman, including the 'Headless Head,' which makes your player appear headless (shown below). On October 31st, 2013, the Headless Horseman avatar bundle was made available on Roblox for the first time.

Roblox accs with headless horseman