When Woody Harrelson was growing up, his father seemed like an ordinary dad.

However, as Woody entered adulthood, it became clear that his father, Charles Harrelson, had a sinister past as a hitman who had been imprisoned multiple times.

Fascinatingly, some of the most captivating actors have complex backgrounds rooted in unusual family dynamics or turbulent childhoods.

This rings especially true for Woody Harrelson, whose father, Charles Harrelson, led a life filled with crime and violence, ultimately earning him the title of a professional hitman who spent a significant portion of his life behind bars.

The year 1968 marked a turning point in Woody Harrelson’s life as his father, Charles, vanished from his world when he was just seven years old.

Subsequently, Charles Harrelson was sentenced to 15 years in prison for the murder of a Texas grain merchant.

Surprisingly, he was released early for good behavior in 1978.

However, Charles Harrelson’s taste of freedom was short-lived as he soon found himself back in trouble with the law.

The Origins of a Hitman

Born on July 24, 1938, in Lovelady, Texas, Charles Voyde Harrelson was the youngest of six siblings in a family where several members were involved in law enforcement.

Despite this background, Charles opted for a criminal path after a brief stint in the U.S. Navy during the 1950s.

After being discharged, Charles Harrelson delved into a life of crime, starting with a robbery charge in Los Angeles in 1959 while working as an encyclopedia salesman.

This marked the beginning of his criminal endeavors, culminating in multiple murder-for-hire schemes in the years following Woody Harrelson’s birth in 1961.

By 1968, Charles had left his family and was deeply involved in gambling in Houston.

His criminal activities escalated, resulting in his arrest multiple times, including two murder charges.

Although acquitted of one murder in 1970, he was convicted in 1973 for the killing of a grain dealer named Sam Degelia Jr.

He received a 15-year sentence but was released after serving only five years due to good behavior.

Despite his time behind bars, Charles Harrelson continued his criminal pursuits and was soon contracted for a high-profile assassination — that of a federal judge.

The Infamous Crime

In 1979, Charles Harrelson was hired by Texas drug lord Jimmy Chagra to eliminate U.S. District Judge John H. Wood Jr., who posed a threat to Chagra’s drug trial.

Nicknamed “Maximum John” for his harsh sentencing of drug offenders, Judge Wood became the target of Harrelson’s deadly mission.

Chagra paid Harrelson $250,000 to carry out the hit, as he faced a lengthy prison term for drug-related charges.

On May 29, 1979, Judge Wood was gunned down outside his San Antonio home by Harrelson using a high-powered rifle equipped with a scope.

This marked the first assassination of a sitting federal judge in U.S. history.

Following a massive manhunt, the FBI apprehended Charles Harrelson in September 1980 after a tense standoff fueled by cocaine-induced erratic behavior.

Woody Harrelson remained unaware of his father’s criminal activities until he stumbled upon a news report about Charles Harrelson’s trial for the judge’s murder in 1981.

Reconnecting with a Troubled Past

Despite their estrangement, Woody Harrelson attempted to establish a relationship with his father in the early 1980s, viewing him more as a potential friend than a paternal figure.

He described his father as articulate, well-read, and charming but acknowledged his absence in his upbringing.

Woody made annual visits to his father in prison after Charles Harrelson was sentenced to two life terms in 1982.

In a surprising turn, Woody stood in for his father during a proxy marriage with a woman he met while incarcerated in 1987, highlighting the complex bond between the father and son.

Notably, Woody invested substantial funds in legal efforts to secure a new trial for his father, underscoring his commitment to Charles despite his criminal past.

Charles Harrelson’s death in 2007 marked the end of a tumultuous chapter in both their lives.

Reflecting on his father’s influence, Woody acknowledged the parallels between them, emphasizing the deep connection they shared despite the stark differences in their paths.

Charles Harrelson’s dark legacy left an indelible mark on Woody, shaping his perspective on life and relationships.

In a poignant conclusion, Woody Harrelson’s journey with his father serves as a testament to the complexities of familial ties and the enduring influence of a troubled past on present-day realities.

The shadow of Charles Harrelson’s actions looms large over Woody’s life, underscoring the intricate interplay between fate, choices, and the enduring bonds of blood.