Weird West: Definitive Edition

Easily done in Grackle. Attack someone and you should commit a Major Crime, at this point the law will try to kill you. Simply leave town, fast travel away slightly to pass time and come back to Grackle. The town should be calm again but you'll be approached by the Sherriff to either pay a fine or serve time. Select the "Go to Jail" option and the achievement will pop. Suggest doing a quick save before committing the initial crime. See the video for more detail: