Snake Jailbird

Snake is Springfield's resident recidivist felon, always getting arrested but never appearing to stay in jail. He speaks with a "Valley Boy" accent and keeps a pack of cigarettes rolled up in his sleeve. He is partial to fast cars and fast women, and has a knack for reckless abandon.

In the episode Treehouse of Horror IX it is revealed that Snake played lacrosse at Ball State University. He also attended Middlebury College and repaid his student loans after robbing Moe Szyslak's tavern. His car's name is "Lil' Bandit", which may be a '68 Pontiac Firebird, or a '69 Dodge Charger. It could be a reference to James Dean's so-called possessed car the "Li'l Bastard". It should be noted that the car's horn plays the opening line of the tune Dixie, similar to The General Lee from the The Dukes of Hazzard.

He has a son who looks just like him, and a brother (or other male relative) who looks and talks very similarly, as seen in an episode where the two run a Three-card Monte game. His ex-girlfriend Gloria briefly dated Charles Montgomery Burns, but then came back to him.

He was once held captive by Herman along with Chief Wiggum (spoof of Pulp Fiction) but was eventually rescued by Kirk and Milhouse Van Houten.

He once ran a telemarketing scam, but could not stick to it because he did not like bothering people at home. He also wrote the books, The Ten Habits of Highly Successful Criminals and A Criminal's Guide to Hiding in Mexico.

In Treehouse of Horror IX, Snake was executed based on a "three-strikes" policy. First he burned down an orphanage, then he blew up a bus full of nuns (which Snake declared was "Totally self-defense"), and finally he smoked in the Kwik-E-Mart. His hair was then implanted into Homer's head, but it had to be removed due to issues with the hair instilling Snake-like characteristics into Homer, e.g. seeking revenge for Snake's imprisonment & execution by murdering Bart etc. This episode was a parody of John Carpenter's 1993 made-for-Showtime film Body Bags, which consisted of multiple stories; in one, Stacey Keach receives a hair transplant with an alien parasite within, and in another, Mark Hamill receives an eye transplant and is taken over by the personality of the eye's previous owner.

Snake's real name, according to an official trading card game, is Chester Turley. However, some of the said cards do have some silly untrue facts which means that the name could be a fake. Snake is also referred to as Jailbird by people who work on the Simpsons.

In the episode The Seemingly Never-Ending Story, Snake referred to himself as Professor Jailbird; it was also revealed that he was formerly an idealistic Indiana Jones-type archaeologist until Moe Szyslak stole the Mayan gold coins he had discovered and was going to donate to the museum, and he decided to take his revenge out on society (convenience stores). In the episode The Wandering Juvie it is stated Snake had previously spend time in a juvenile facility, suggesting he was a criminal before being an archaeologist. In the flashback episode Springfield Up a teen-aged Snake is called "Detention Bird" by a 16-year-old Clancy Wiggum

In Pygmoelian, it was also revealed that Snake had a son. The Seemingly Never-Ending Story revealed that his son's name is Jeremy. The episode also reveals that Snake has custody issues with his son. Although Snake seems to have committed every crime possible, he is an extremely good father to Jeremy. He points Bart out to Jeremy, saying, "Look, there's a boy you can play with!" Bart and Jeremy play Battleship for the remainder of the episode.