The Mysterious Disappearance of Wintertime

– Written by Will Barber –

Recently I was going through one of my old playlists from 2017 and I came across the song “Me & Ben”. I hadn’t heard the song in so long I almost didn’t recognize it and then I saw it was by Wintertime and all the memories flooded in. I then went and relistened to his very short catalogue and realized how much he shaped my introduction to the SoundCloud cloud rap scene. His laid back cadence and ethereal beat selection was so unique and unlike anything I had heard at the time. Wintertime’s career is one of the most interesting in the underground rap scene because despite his rising success, he made the unexpected decision to stop releasing music entirely.

Despite having a very short career, Wintertime’s influence was undeniable and a pillar of the 2016-2017 soundcloud rap scene. Originally releasing music under the name Wintertime Zi, he made his debut on SoundCloud in 2015 with You Can Go. His breakthrough came with Thru It All, a song that later received a remix featuring iLoveMakonnen. He also joined forces with other upcoming rapper Lil Yachty to drop the collaboration “Wintertime on a Boat”. He would drop solo projects “I Know What You Did Last Winter” and his self-titled mixtape which solidified his career in the underground and even saw him reaching mainstream with the track “All The Time 2”. His music was gaining traction, his fanbase was growing, and all signs pointed toward a promising future.

Then, he disappeared.

Wintertime has not dropped any music since July of 2017 except for a feature verse on Ugly Gods 2019 album “Bumps & Bruises”. It has fans confused as to why such an influential upcoming rapper would disappear amidst his big break. And no, it’s not because spring came…

Wintertime has always been known for his private nature, rarely engaging on social media or responding to comments and direct messages, making it extremely difficult for me to uncover any personal details about him. He has kept his life so private that even his real name remains unknown. There is no confirmed reasoning behind his disappearance but after scouring google, reddit threads, and youtube videos, the only explanation is that he is a private guy who never really wanted fame.

The last few signs of Wintertime were very cryptic. His last instagram post was in 2019 where he is seen standing on the top of stairs of a house wearing a ski mask holding a backpack staring into the camera. The caption states that he would be returning to America after living in Iceland for 2 years in isolation surrounded by only his thoughts. He also mentioned in this post that he was going to be writing a book on this experience but as we know this never happened. The last time we’ve heard from him since this post was on twitter in 2021 where he says “MARCH 3021”. Of course both of these posts have since been deleted and all of his social media has been wiped completely empty.

The idea that Wintertime just didn’t like being in the spotlight is the most plausible explanation for his disappearance. He probably earned enough money to live comfortably and chose to completely avoid the public eye. 

Despite his absence, his legacy remains and fans still speculate about a possible comeback. Whether he ever returns or remains a mystery, Wintertime’s impact on the SoundCloud era of rap is undeniable.