Inside the Life of Diane Lou Oswald, Woody Harrelson’s Mom

By RahulPublished on: March 13, 2024 Updated on: June 4, 2024
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Diane Lou Oswald, Woody Harrelson’s mother, emerges from the shadows of her son’s stellar career with a story that could rival any Hollywood script. Beyond her connection to Woody’s success in the film industry, Diane’s life has been marked by profound complexities, notably her marriage to Charles Harrelson, a man later convicted as a contract killer.

She raised three children, Woody, Brett, and Jordan Harrelson, as a single mom, working as a legal secretary and barely making enough money to get by. Life was tough for her, juggling work and taking care of three boys. On top of all that, Diane had to deal with the fact that her late husband was in jail.

Besides, various sources think Diane is related to Lee Harvey Oswald, but they are not. The only similarity they have between them is their surname.

Adding to the intrigue, a disclosure by actor Matthew McConaughey has hinted at a surprising twist. He said that his mom has revealed a past encounter with Charles, suggesting the possibility that McConaughey could be Diane’s stepsons. This web of personal histories and connections adds a layer of mystery to the life of Diane.

Her Husband Charles Was a Hitman

Diane married Charles somewhat spontaneously when he was on Navy leave in Houston in 1959. They were together until the year 1964. During their marriage, Diane supported Charles through various challenges, including a prison term for theft in California in 1960.

Her late ex-husband led a troubled life, working jobs like an encyclopedia salesman and professional gambler, but his path darkened when he was convicted of armed robbery in 1960. His criminal activities escalated as he claimed involvement in numerous murders from the early 1960s.

The marriage faced its ultimate test when Charles disappeared from the family’s life in Houston in 1968, leaving Diane to raise their three children alone. Charles’s life of crime culminated in his involvement in high-profile cases, including the murder-for-hire killing of Judge John H. Wood Jr.

A photo of Woody and his dad Charles
Diane’s ex-husband Charles (right) was a hitman.

Though Charles was arrested, Diane had already been facing the reality of raising their children without him for years.

Despite the turmoil and the challenges, she chose to keep her children shielded from the grim realities of their father’s criminal activities. She never spoke ill of Charles to their sons, nor did she divulge the depth of his crimes.

This silence extended to the point where, upon hearing news of their father’s involvement in a high-profile murder, her son Woody confronted her with questions.

However, Diane remained tight-lipped, and said, “How many Charles V. Harrelsons can there be?” This left her children to grapple with the possibility and realization on their own, as Woody did when he pieced together that the man charged with a heinous crime was indeed their father.

In 2007, Charles, estranged ex-husband of Diane, passed away at the age of 69. His death was due to a heart attack, an event that marked the end of a turbulent and notorious life. Prior to his passing, Charles had faced health challenges, including a battle with cancer.

Diane Moved To Lebanon with her Kids in the 70s

In 1973, Oswald decided to move back to her hometown, Lebanon, Ohio, with her three sons. This was a big deal because they were leaving behind everything that happened in Texas.

Diane grew up in Lebanon, so it was like a fresh start for her and her kids. They got to go to a new school there and have a normal life.

Diane’s mom, Mary Lou Lauterwasser, was really important when they moved back. Since Diane’s dad, Kenneth Earl Oswald, passed away way back in 1957, he wasn’t around when they moved. But even so, Diane’s mom and her grandma were there to help out with Woody and his brothers.

Oswald and Woody attending an event
Diane was a super mom to her sons.

In an interview with GQ, Woody talked about his great-grandma Polly being super fun and telling great stories. He said his grandma was quieter, but still a big part of their lives.

Additionally, Oswald also brought her kids as a Presbyterian, however, Woody changed his views and became more progressive later. Nevertheless, Diane, to this day, considers herself a devout Presbyterian.

Time was tough for the Harrelson clan, as Diane’s job was merely keeping food on the table. All of her boys were going to school, and Woody especially was making tremendous strides. Woody once told that back then he was the most popular guy in school, which made his mother proud.

She Has Influenced Her Sons In a Lot of Ways

Woody Harrelson’s bond with his mother, Diane, is deeply influential and supportive. Oswald has been proud since Woody’s early days, particularly when he received an Oscar nomination for The Messenger.

Harrelson shares that receiving his mother’s approval, especially after being nominated alongside Christopher Plummer for an Oscar, was deeply fulfilling for him, emphasizing that her recognition meant more to him than winning any award.

Diane's sons Woody (Left) and Bret (Right).
Diane’s sons Woody (Left) and Brett (Right).

Additionally, Woody credits her for instilling in him compassion for the world and nature, as well as a strong work ethic. Due to this, Harrelson became a Vegan. Furthermore, PETA named him in their 2012 Sexiest Vegetarians List.

Aside from Woody, her son Brett is also an actor. He later became Woody’s assistant. Meanwhile, Jordan didn’t follow his brother’s suit and instead worked as an Insurance broker.

Matthew McConaughey Said Diane’s late Ex-Husband Charles Might Be His Dad

The claim by Matthew regarding his potential familial ties with Woody presents an intriguing narrative. McConaughey suggested that he and Harrelson could be half-brothers, stemming from the possibility that Charles Harrelson, Woody’s father, could also be his.

This speculation arises from revelations by McConaughey’s mother, who admitted to having known Charles around the time Matthew was conceived.

The two actors, already close, discussed undergoing a DNA test to determine the truth of this familial connection. However, for Matthew, it is a much more big deal. Harrelson told Stephen Colbert,

“But for him, it’s a much more big deal. I mean, he feels like he’s losing a father. But I’m like, no you’re gaining a different father and a brother.”

What Is Diane Doing Today?

Diane Lou Oswald is currently 87 years old. At this stage in her life, she is likely enjoying her retirement in Lebanon, surrounded by her family, including her grandchildren.

She has three granddaughters from Woody’s side, Deni Harrelson, Zoe Harrelson, and Makani Harrelson.

Meanwhile, she last appeared in the public in 2017. She went to London to attend The Wimbledon Championships with her son Woody.

About Author: Rahul

Rahul has been diving into the world of entertainment in niches like celebrity, anime, and health articles since 2016. As a passionate writer, he combines personal experiences with thorough research to create content that's not only informative but also relatable and engaging.