Tyler Gregory Okonma a.k.a. Tyler, the Creator was arrested on March 15th, 2014 for taking part in a riot.
A mugshot was taken afterwards, and the internet naturally caught up the image instantly, creating huge hype around the whole story.
Only one day following the arrest, the original image was posted to /r/ photoshopbattles.
A lot of creative interpretations were submitted. These images eventually gave foundations to a number of other memes.
During the next few years the meme made appearances mostly in /r/ tylerthecreator.
Eventually in 2019 hip hop and rap communities started utilizing the Tyler, the Creator mugshot as an ironic meme template.
The format was also featured in a number of occasions on iFunny and Instagram meme pages.