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Bobby Charles is a character role-played by 25Daves.

General Description[]

Bobby Charles is known for his frequent shenanigans and get-rich quick schemes, he is a conniving man who has very obscured morals and only does "good" things when it financially benefits him. When Bobby is involved in illegal activity and people question his morality and principles, he repeats "I AM A DEVOUT CATHOLIC THAT GOES TO MASS EVERY SUNDAY". Most schemes that Bobby cooks up land him in legal trouble, making him a frequent target of criticism and hatred from the LSPD.

During Vivek Ramasquamy's mayoral campaign, Bobby became enthralled with Vivek's campaign messages, promptly joining as a bodyguard and political advisor. Bobby views Vivek as a god-like figure, willing to do any and everything for him, even to the point of landing in legal or financial trouble.

On 12/27/23, he was embroiled in a political controversy when he was stabbed by Lilith Fulker, Vivek’s mayoral campaign manager at Chumash Pier. Remaining loyal to the campaign, Bobby decided to testify in his own attempted murderers' defense, which ultimately would fail.

By 2024, Bobby had begun considering a run for Mayor, against his opponents, Maximilian Thoroughbred, Party Hardy, Pilbis Toretti, Donnie McMuffin, Stelio Lambros, Michael Simone, Jebediah "Beef" von Wunder, Eugene Zuckerberg, Ronald Rump, and Cletus Cornwood. He hesitated, but decided to file an application to make it official, unfortunately for him on the 19th of July 2024 his dream had been failed as a Mayor of Blaine County, because Andy Jones had won the elections of it.

Eventually, Bobby's lifelong dream came true: he was finally appointed warden of Bolingbroke Penitentiary along with Carmine Costello, whom the duo promptly re-named to Dog Town.

Warden of Bolingbroke "Dog Town"[]

Around February of 2024, mayor Maximilian Thoroughbred began dropping subtle hints that Bobby and Carmine might be soon appointed wardens of Bolingbroke, the reason being two-fold: One, because no-one better suited would want to run the prison, and two being a way to keep them productive in the hopes of reducing their shenanigans within the city. The city council of 8 ultimately decided to test a brand new method of running the prison from years past, being as follows:

  • Bolingbroke would be considered a "lawless" land, where the wardens would be forced to put the law into their own hands in dealing with inmates and potential intruders into the prison.
  • No armory or government equipment would be provided to prison staff out of fear of being misused or stolen.

On March 2nd, Carmine and Bobby received badges and keys to the prison, deciding that Bolingbroke would henceforth be known as "Dog Town," and all prisoners would be referred to as "Maggots."

Rank Insignia Note Date
Warden Warden Appointed as Warden with Carmine Costello; Badge #25 March 2nd, 2024

Friends and Allies[]


  • His State ID is 1666.
  • Set up a phone sex hotline in 2024 in a money making effort, acting as an "anime gamer girl or gamer femboy," depending on the callers' preference. While he charges $50 a minute for these calls and gets them frequently, he is almost never actually paid for these services.
  • On 1/19/24 Bobby Charles's faked his death in hope that he would be able to collect donations and profit from the funeral.