Gary Ray Bowles was born on January 25, 1962, in Clifton Forge, Virginia. His father died before he was born, and his mother remarried several times. Gary's stepfathers were often abusive, creating a challenging and unstable home environment that deeply affected him.

At the age of 11, Gary ran away from home to escape the abuse. He spent his teenage years living on the streets, learning to survive on his own. During this time, he struggled with homelessness and poverty, often resorting to crime to make ends meet. Despite his difficult circumstances, Gary found work in various odd jobs, though none of them lasted long.

Gary's early life was marked by instability and a lack of support. Without a stable home or guidance, he turned to drugs and alcohol to cope with his feelings of abandonment and pain. These habits worsened his situation, leading to further trouble with the law.

As he entered adulthood, Gary's problems escalated. He was arrested multiple times for theft, assault, and other crimes. The absence of positive influences or a support system made it difficult for him to escape the cycle of crime and addiction.

On March 15, 1994, in Daytona Beach, Florida, Gary Ray Bowles committed his first known murder. His victim was 59-year-old John Hardy Roberts, who had kindly offered Bowles a place to stay. Bowles beat and strangled Roberts to death, then stole his credit card, which he later used in Kingsland, Georgia, and Nashville, Tennessee. The police quickly identified Bowles as a suspect after finding his fingerprints and probation records at the crime scene.

Over the next six months, Bowles murdered four more men. His victims included 39-year-old David Jarman in Wheaton, Maryland, 72-year-old Milton Bradley in Savannah, Georgia, 47-year-old Alverson Carter Jr. in Atlanta, Georgia, and 37-year-old Albert Morris in Hilliard, Florida. Bowles typically prostituted himself to his victims before beating and strangling them, then stealing their credit cards.

While evading capture, Bowles was placed on the FBI's list of the country’s 10 Most Wanted Fugitives. On November 22, 1994, he was arrested for the murder of Walter Jamelle "Jay" Hinton in Jacksonville Beach, Florida, and confessed to all six murders.

After his arrest, Bowles explained to the police that he had moved to Daytona Beach after his release from prison in 1991. He lived with a girlfriend and resumed working as a prostitute. His girlfriend became pregnant but had an abortion after discovering Bowles was a sex worker. Bowles told the police that he blamed gay men for the abortion, which drove him to become a murderer.

In May 1996, Bowles pleaded guilty to killing Walter Jamelle Hinton in Jacksonville on November 17, 1994. He killed Hinton by hitting his head with a 40-pound stepping stone while Hinton slept and stuffing a towel down his throat during the struggle. Bowles received the death penalty for Hinton's murder. In August 1997, while on death row for Hinton's murder, Bowles pleaded guilty to beating and strangling John Hardy Roberts in 1994.

Bowles was found guilty of three counts of murder and sentenced to death. However, the Florida Supreme Court reversed the sentence, ruling that the court had erred by allowing the jury to hear that Bowles hated homosexuals and that the victim was gay. After a new sentencing hearing in 1999, Bowles was again given the death penalty.

Gary Ray Bowles was executed by lethal injection on August 22, 2019, at Florida State Prison in Raiford. For his last meal, he ate three cheeseburgers, french fries, and bacon. Bowles was the last person executed in Florida until the execution of Donald Dillbeck on February 23, 2023.