Diane Lou Oswald: Woody Harrelson’s Mother and the Family’s Darkest Chapter

Diane Lou Oswald is a private American woman known publicly for one reason: she is the mother of actor Woody Harrelson, and the ex-wife of Charles Harrelson, the man convicted of assassinating a federal judge. She has never sought public attention herself, but her story intersects with one of the more startling true-crime cases of the late 20th century.

Background

Oswald was born in 1937 in Lebanon, a small town in Warren County, Ohio, to parents Kenneth and Mary Lou Oswald. She grew up in a close-knit Midwestern community and later worked as a secretary to support her family.

In 1959, she married Charles Voyde Harrelson, who was at the time working as an encyclopedia salesman and card gambler. According to Wikipedia’s entry on Charles Harrelson, which lists his several marriages, Oswald was his second wife. The couple had three sons together: Woody, Brett, and Jordan.

The Charles Harrelson Case

The marriage did not last. Oswald and Charles Harrelson divorced in 1964, five years after they wed, and she was left to raise their three young sons largely on her own. She later moved the family back to her hometown of Lebanon, Ohio, where Woody went on to finish high school.

Charles Harrelson’s life took a far darker turn after the split. He was convicted of a 1968 murder-for-hire killing in Texas and served time before being paroled in 1978. The following year, on May 29, 1979, U.S. District Judge John H. Wood Jr. was shot and killed outside his San Antonio home, the first sitting federal judge assassinated in the 20th century. Investigators determined that Harrelson had been paid roughly $250,000 by drug trafficker Jamiel “Jimmy” Chagra to carry out the killing, according to reporting from Texas Monthly and History.com.

Harrelson was convicted of the murder in December 1982 and sentenced to two life terms. He died in prison on March 15, 2007, at age 69, reportedly of heart disease, per Snopes’ reporting on the case.

Woody Harrelson has spoken about his complicated relationship with his father over the years, visiting him in prison and even funding legal efforts to appeal the conviction, though those efforts did not succeed.

Raising Her Sons

After the divorce, Oswald worked steadily to provide for her three boys. Multiple accounts describe her as the steadying presence in their lives during a period when their father’s crimes were making national headlines. Woody Harrelson has credited her, rather than his father, with shaping his character.

What Woody Harrelson Has Said About Her

Harrelson has spoken warmly about his mother in interviews over the years. In a 2018 interview with The Guardian, he described her as a major positive influence who taught him to treat people well and behave honorably, adding that she remains a role model for that today. In an earlier interview with GQ, he credited her with passing on her energy and work ethic, joking that he has “a better play ethic” than she does.

Oswald has occasionally appeared alongside her son at public events, including film premieres, but has otherwise kept a low public profile, consistent with the private life she has maintained throughout her adult years.