Oscar Ray Bolin was born on January 22, 1962, in Portland, Indiana. His family, consisting of laborers and carnival workers, moved across several states including Florida, Indiana, Kentucky, and Ohio. Bolin's childhood was troubled; his father often beat him, and his mother once led him to the school bus stop on a leash.

During his youth, Bolin frequently got into trouble with the law. At 15, he committed theft in Ohio and was arrested. In the early 1980s, he moved to Florida and began working as a carnival worker.

In 1982, his girlfriend, Cheryl Haffner, reported that Bolin had kidnapped her and driven her around the Tampa Bay area for hours. Although he was arrested for false imprisonment, the charge was later dropped.

Despite this incident, Bolin and Haffner got married in 1983 in Hillsborough County, Florida.

On January 25, 1986, 25-year-old Natalie Blanche Holley finished her shift as a night manager at a Church's Fried Chicken restaurant in Tampa. She left the store around 1:30 a.m., and her body was found hours later by a jogger. She had been stabbed to death.

On November 5, 1986, 17-year-old Stephanie Collins, a high school student, disappeared after her shift at a drug store. A month later, her body was found wrapped in sheets and towels. She had been stabbed and her skull was crushed.

The same day Collins' body was found, 26-year-old Teri Lynn Matthews went missing. Her car was discovered outside a post office with the engine running. Her body was found in the woods, wrapped in a white sheet, with her throat cut and her body beaten.

In 1987, Bolin and two other men kidnapped and raped a waitress in Ohio. Bolin attempted to kill her, but the gun jammed, and he let her go. He was captured and sentenced to 22 to 75 years in prison.

In 1989, Bolin's ex-wife told her new husband about Bolin's confessions of multiple murders. Her husband called a tip line, leading to Bolin's arrest. Witnesses, including Bolin's half-brother and cousin, testified against him, providing details of his crimes.

Bolin was found guilty of the murders and received death sentences for the killings of Holley, Collins, and Matthews. He maintained his innocence until the end.

On January 7, 2016, Bolin was executed by lethal injection. He was the first person executed in the United States in 2016. He declined to make a final statement but enjoyed a last meal of rib-eye steak, a baked potato, salad, garlic bread, lemon meringue pie, and Coca-Cola.