User is an object character that appeared in jacknjellify's community tab, which appears to be based on the default YouTube profile icon. They appeared next to Loser in an image asking whether the reader was a Loser or a User.
Pumpkin is the only character by Jacknjellify to be introduced in 2014.
Pumpkin is yet to reappear in any sort of BFDI related media.
Other characters that appear in the image are the 22 contestants from BFDIA, a skeleton head, a bone, Woody, a thing that is eating Yellow Face, and a circle with arms and legs (the circle might be another Coiny)
Drear-Top is an object character that appeared on Michael Huang's Twitter account on a tweet from March 10th, 2020. They are a version of Teardrop with their asset turned upside down and their face is moved towards what would be Teardrop's base.
Despite the claim in the tweet that Drear-Top is BFDI's first hyphenated character, 8-Ball has been a contestant for 3 years before the tweet had been posted.