Robert Charles Gleason Jr. was born on April 10, 1970, in Lowell, Massachusetts. He grew up in a troubled environment. His family faced difficulties that affected his childhood. Specific details about his early family life are not widely available, but it is known that he had a difficult upbringing.

As a teenager, Gleason moved with his family to Virginia. He struggled with issues at school and with authority figures. His early years showed signs of a troubled adolescent life. By the time he reached adulthood, he found himself involved in criminal activities.

Gleason's criminal acts began before he became a serial killer. His early life set the stage for many of the choices he made later on. Despite a challenging start, the specifics of his youth remain somewhat unclear. What is known is that he would eventually face serious consequences for his actions.

Robert Charles Gleason Jr. was involved in several serious crimes while in prison. In 2007, he murdered Michael Kent Jamerson in Amherst County, Virginia. This murder took place to hide his ties to a drug gang. For this crime, Gleason was sentenced to life in prison in 2008.

While serving his life sentence at Wallens Ridge State Prison, Gleason became angry with his severely mentally ill cellmate, Harvey Gray Watson. Watson was serving a 100-year sentence for a shooting spree that had happened in 1983. On May 8, 2009, the second anniversary of Jamerson's death, Gleason attacked Watson. He hog-tied him, beat him, and then strangled him. Gleason later admitted to this crime in court and stated he would continue to kill if he was not given a death sentence.

Gleason claimed to have committed more murders prior to being in prison. He said he had been paid to kill some of the people and killed others because they upset him.

Later, while at Red Onion State Prison, Gleason killed another inmate named Aaron Cooper on July 28, 2010. Cooper was serving time for robbery. Gleason strangled him through wire fencing that divided their cages in the prison yard.

As a result of these additional murders, Gleason was sentenced to death in 2011. He chose to waive his appeals and requested to be executed by electric chair instead of lethal injection.

Gleason was executed on January 16, 2013, at Greensville Correctional Center in Jarratt, Virginia. His execution made him the first person executed in the United States in 2013. Before his death, he requested a last meal that he wanted kept secret and made a statement that included an Irish phrase which translates to "Kiss my arse."

His execution was significant because he was the last person to be put to death by electric chair in Virginia. In 2021, Virginia abolished capital punishment, marking the end of the electric chair as a method of execution in the state.