Diane Lou Oswald: A Mother’s Love, Influence, and A Legacy of Strength

Diane Lou Oswald, an American native, is widely recognized as the mother of the renowned Hollywood actor and playwright Woody Harrelson. However, her own story is one of hard work and dedication. Before she became known as a celebrity parent, Diane excelled as a secretary, showcasing her commitment and professionalism in her career.

A woman of strong religious faith, Diane Lou Oswald played a pivotal role in shaping her son’s path to success. She not only provided love and support but also instilled in him her values of resilience and determination. Her influence extended beyond her immediate family, inspiring many with her story of perseverance and strength.

Despite not being in the limelight, Diane Lou Oswald’s impact on those around her, especially her children, is undeniable. Her life serves as a testament to the power of a mother’s love and guidance in shaping the future of those she holds dear.

Profile Summary of Diane Lou Oswald

Full/Real name Diane Lou Oswald
Birth date 1937
Death date2020
BirthplaceLebanon, Warren, Ohio, United States
Age 83 years old (At the time of death)
Ethnicity Caucasian
Sexual OrientationStraight
FatherKenneth Oswald
MotherMary Lou Oswald
SiblingsNot Revealed
Marital statusFormerly married 
SpouseCharles Harrelson (m. 1959–1964)
ChildrenWoody Harrelson, Brett Harrelson, Jordan Harrelson
GrandchildrenZoe Giordano Harrelson and Deni Montana Harrelson, Makani Ravello Harrelson
Famous ForBeing the Woody Harrelson’s Mother
Height5’6″, 167cm
Weight55Kg, 121lbs
Body Measurements32-24-34 inch
EducationCompleted education at a public high school
ProfessionMother of actor and playwright Woody Harrelson
Net Worth Approximately $1 million US dollars

Diane Lou Oswald Biography

Diane Lou Oswald, born in 1937 in Lebanon, Warren, Ohio, embodied remarkable resilience and strength throughout her life. As a legal secretary, she excelled in her profession, demonstrating unwavering attention to detail and organizational skills that went beyond the confines of her workplace.

Diane Lou Oswald Biography
Google has well-covered Diane Lou Oswald.

However, her life took on a unique dimension as the mother of Hollywood actor Woody Harrelson. Despite facing the complexities of a controversial marriage to Charles V. Harrelson, a convicted contract killer, Diane emerged as a resilient single mother, raising three sons—Woody, Brett, and Jordan—with love and determination.

Her enduring impact on Woody’s successful acting career and the values she instilled in her children highlight the profound influence of a woman whose legacy transcends the ordinary, leaving an indelible mark on those she touched. Diane Lou Oswald’s life story serves as a testament to the power of resilience, love, and the enduring impact of a mother’s guidance.

Diane Lou Oswald Family

Diane Lou Oswald Family

Diane Lou Oswald’s journey began in the small town of Lebanon, Warren, Ohio, in 1937, where she was raised in the warmth of an upper-middle-class family. Her formative years in this close-knit community laid the foundation for the strength and resilience that would define her character.

Born to Kenneth and Mary Lou Oswald, Diane inherited a strong sense of determination and compassion from her family. These values became guiding principles in her life, shaping her into the dedicated legal secretary, loving mother, and inspiring figure she would become.

As Diane grew up, she embraced these values, carrying them with her as she pursued her career and raised her family. Her story is a testament to the lasting impact of a supportive family and the strength that comes from embracing one’s roots.

Meet Diane Lou Oswald’s parents

Diane Lou Oswald’s life story is deeply intertwined with the lives of her parents, Kenneth and Mary Lou Oswald. Born in 1937, Diane was raised in a loving family environment, nurtured by the values instilled by her parents. Her father, Kenneth Earl Oswald, born in 1912, played a significant role in shaping her early years before his passing in 1957. Her mother, Mary Lou Oswald, born in 1915, continued to be a pillar of strength and support for Diane until her passing in 2000.

Kenneth Oswald’s lineage traces back to Dutch and Izora Oswald, highlighting the rich family history that Diane was born into. Diane embodied the values of resilience, compassion, and determination, which can be traced back to her upbringing and the strong foundation laid by her parents. Despite the challenges and losses she faced, Diane’s life is a testament to the enduring influence of family and the profound impact of parental love and guidance.

Diane Lou Oswald Professional Life as a Legal Secretary

Diane Lou Oswald’s professional journey led her into the legal field, where her meticulous attention to detail and exceptional organizational skills paved the way for success as a legal secretary. This phase of her life not only showcased her professional acumen but also laid the groundwork for her role as a devoted mother.

The skills Diane honed as a legal secretary extended far beyond the office walls, shaping her approach to life’s challenges. Her ability to navigate difficulties with grace and efficiency and her knack for organization became the pillars of her resilience in the face of personal struggles. These qualities not only defined her professional success but also influenced her role as a mother, instilling in her children the values of perseverance and determination.

Diane Lou Oswald’s journey as a legal secretary exemplifies the transformative power of hard work and dedication. Her story serves as a testament to the lasting impact of a strong work ethic and the importance of facing life’s challenges with resilience and grace.

Diane Lou Oswald’s Husband Convicted Hitman, Charles Harrelson

Diane Lou Oswald’s Husband Convicted Hitman, Charles Harrelson

Diane Lou Oswald’s former husband, Charles Boyd Harrelson, led a life marked by crime and controversy. Known as an American hitman and organized crime figure, he gained notoriety for his involvement in the assassination of federal judge John H. Wood Jr., making him the first federal judge to be assassinated in the 20th century.

Charles Harrelson’s criminal activities extended beyond the assassination. He worked as an encyclopedia salesman in California and also pursued a career as a professional gambler. His criminal record included a conviction for armed robbery in 1960, and he later admitted to being involved in numerous murders dating back to the early 1960s.

Despite their marriage in 1959, Diane and Charles’s relationship was short-lived, ending in separation in 1964. Charles Harrelson’s life came to a close when he was found dead in his cell on March 15, 2007, at the age of 68, succumbing to a heart attack. His death marked the end of a tumultuous and criminal-filled life, leaving behind a legacy of infamy and intrigue.

Diane Lou Oswald Marriage Controversy

Diane Lou Oswald Marriage Controversy

Diane Lou Oswald’s marital journey was fraught with controversy, as she was married to Charles Harrelson, a convicted contract killer. This tumultuous relationship presented numerous challenges that deeply impacted her life.

Despite the difficulties, Diane showed remarkable resilience and strength. Following their divorce, she single-handedly raised three sons, demonstrating her unwavering commitment to her children’s well-being.

Diane’s story is one of courage and perseverance, serving as an inspiration to many. Her ability to navigate through a controversial marriage while raising her sons alone is a testament to her character and determination. Her story resonates with audiences, showcasing the power of resilience in the face of adversity.

Diane Lou Oswald Children

Diane Lou Oswald Children

Diane Lou Oswald’s children have made a name for themselves in the entertainment industry. Brett Harrelson, Woody Harrelson, and Jordan Harrelson have all pursued acting careers, following in their parents’ footsteps.

Woody Harrelson, born Woodrow Tracy Harrelson, has achieved significant success with roles in films such as “The People vs. Larry Flynt,” “The Messenger,” and “Three Billboards Outside Ebbing, Missouri.” He is also known for his portrayal of Haymitch Abernathy in “The Hunger Games” film series.

Brett Harrelson, the second son, has also made a mark in the acting world. Jordan Harrelson, the youngest of the three, has showcased his talent in various roles, including in “Between the Stars,” “Well,” and “Broken Promise.” The Harrelson siblings’ achievements highlight their talent and dedication to their craft, continuing their family’s legacy in the entertainment industry.

Diane Lou Oswald raised her children alone

Diane Lou Oswald raised her children alone

Diane Lou Oswald’s strength and resilience were truly remarkable, as she raised her three children alone after separating from her husband, Charles Harrelson, in 1964. The family faced further challenges when Charles disappeared from their home in Houston in 1968, leaving Diane to shoulder the responsibility of caring for their children.

Despite the difficult circumstances and the actions of her husband, Diane never spoke ill of Charles to her children. Woody Harrelson, in particular, maintained a complex relationship with his father, visiting him regularly in federal prison after Charles was arrested and convicted of the murder of Judge Wood in 1981.

Diane’s unwavering support for her children and her ability to maintain a sense of compassion and understanding even in the face of adversity is a testament to her strength of character. Her story is a reminder of the enduring power of a mother’s love and her willingness to sacrifice for the well-being of her family.

Diane Lou Oswald has three grandchildren

Diane Lou Oswald’s family history is rooted in her grandparents, Dutch and Izora Oswald, who laid the foundation for her lineage. Her parents, Kenneth Oswald and Mary Lou Oswald, raised her with love and care, instilling in her the values that would shape her life. Diane’s journey took a significant turn when she met and partnered with Charles Harrelson, with whom she welcomed three children: Brett Harrelson, Woody Harrelson, and Jordan Harrelson. This family tree represents a rich tapestry of experiences, with each member contributing to its vibrant history.

The next generation of the Oswald-Harrelson family includes Diane’s grandchildren: Deni Harrelson, Zoe Harrelson, and Makani Harrelson. These young individuals carry forward the legacy of their ancestors, embodying the values of resilience, determination, and compassion that their ancestors passed down through the generations. Diane’s family tree is a testament to the enduring bonds of family and the profound impact each member can have on shaping the future.

Diane Lou Oswald Her ex-husband was a contract killer

Diane Lou Oswald Her ex-husband was a contract killer

Diane Lou Oswald’s marriage to Charles Harrelson became tumultuous as Charles descended into criminal activities, eventually leading to his notoriety as a contract killer. Despite their initial years together and the birth of their three children, their relationship began to unravel, and Charles left the family home in 1964. This departure marked the beginning of a challenging period for Diane as she navigated the complexities of raising their children alone while dealing with the fallout of her ex-husband’s criminal activities.

Charles Harrelson’s involvement in crime continued to escalate after their separation, culminating in his conviction for the murder of US District Judge John H. Wood Jr. While Charles faced legal battles and convictions for various crimes, including the murder-for-hire killing of Sam Degelia Jr., Diane remained steadfast in her commitment to her children, never turning them against their father. Despite the challenges she faced, Diane’s strength and resilience shone through as she persevered in providing a stable and loving environment for her family.

Diane Lou Oswald’s Famous Son, Woody Harrelson

Diane Lou Oswald’s Famous Son, Woody Harrelson

Diane Lou Oswald’s son, Woodrow Tracy Harrelson, is a renowned actor and playwright, born on July 23, 1961, in Midland, Texas, USA. Growing up in Lebanon, Ohio, where Diane was from, Woody has made a significant mark in the film and television industry over the past 30 years, establishing himself as one of the most acclaimed actors of his generation.

Aside from his successful acting career, Woody’s ventures into playwriting have also contributed to his wealth and reputation. He holds degrees in theater arts and English from Hanover College and gained valuable experience in New York theater. Woody attended Lebanon High School, graduating in 1979, before pursuing further education at Hanover College in Hanover, Indiana.

Woody Harrelson first gained widespread recognition for his role as bartender Woody Boyd on the NBC sitcom Cheers (1985–1993). He has since delivered memorable performances in films such as “White Men Can’t Jump,” “The Hunger Games,” “The People vs. Larry Flynt,” and “Kingpin,” earning numerous award nominations and wins, including a Primetime Emmy Award and two Screen Actors Guild Awards.

Woody also advocates for the legalization of marijuana and hemp, often participating in environmental events to promote sustainable practices. In his personal life, Woody Harrelson briefly married Nancy Simon in the 1980s before tying the knot with his former assistant, Laura Louie. The couple has three daughters together—Makani, Zoe, and Dani—forming a loving family that complements Woody’s successful career in the entertainment industry.

Influence on Woody Harrelson

Influence on Woody Harrelson

Diane Lou Oswald’s influence on Woody Harrelson, the acclaimed Hollywood actor, was profound and enduring. Woody often reflects on the supportive and loving bond they shared, which played a crucial role in shaping his perspective on success, gratitude, and the importance of family. Diane’s notes expressing joy during significant moments in Woody’s career, such as his Oscar nomination, underscored the pride she took in her son’s achievements.

Her emotional connection with Woody went beyond Hollywood accolades, shaping his worldview and contributing to his success as an actor. Woody attributes his strong work ethic and deep love for nature to the values instilled by his mother, highlighting the lasting impact of her influence on his life and career. Diane Lou Oswald’s role as a supportive and loving mother inspires Woody and serves as a testament to the profound impact a parent can have on their child’s life.

Diane Lou Oswald’s Numerous Achievements

EntrepreneurshipEarly ventures into business
WritingRenowned writer and artist
ArtCritical acclaim for compelling artwork
LeadershipRecognized for innovative ideas and leadership

Diane Lou Oswald is a multifaceted woman whose remarkable achievements have left a lasting impact in various fields. Her story serves as an inspiration, showcasing her adaptability and tenacity.

Diane has excelled in numerous areas throughout her career, demonstrating her versatility and skill. From her early entrepreneurial ventures to her later success as a renowned writer and artist, Diane’s journey reflects a life of remarkable achievement.

Her list of accolades is extensive, recognizing her innovative ideas and leadership in the business world, as well as her artistic talents, which have earned critical acclaim. Diane’s ability to captivate others, whether through her language or her artwork, sets her apart as a truly talented and accomplished individual deserving of recognition and celebration.

Diane Lou Oswald Personal Attributes and Hobbies

Personal Attributes
Favorite SportsCricket & Hockey
Favorite CityLos Angeles, United States
HobbiesGardening, Listening to Music, Traveling

Diane Lou Oswald’s interests and hobbies were integral to her identity, adding depth to her character beyond her roles as a legal secretary and mother. She had a fondness for gardening, which not only brought her joy but also contributed to creating a nurturing environment for her children. Her love for music and travel provided avenues for exploration and relaxation, enriching her life and the lives of those around her. Additionally, her fondness for the city of Los Angeles, United States, suggests a connection to the vibrant culture and lifestyle that the city embodies. Diane’s multifaceted personality and interests helped shape the environment in which her family thrived, leaving a lasting impact on all who knew her.

Diane Lou Oswald’s Net Worth

Diane Lou Oswald's Net Worth

Diane Lou Oswald’s impact transcends mere financial wealth, with her reported net worth estimated at around $1 million. Her true riches lie in the legacy she crafted through her life’s work and the values she instilled in her children. Beyond the numbers, Diane’s influence continues to resonate through the successful careers and the strong moral compass exhibited by her sons.

Her legacy is visible in the accomplishments of her children, particularly Woody Harrelson’s illustrious acting career. The values of resilience, compassion, and determination that Diane imparted are evident in the way her sons navigate their lives and careers. Her love and guidance continue to shape their paths, serving as a testament to her enduring influence.

Through Woody, Brett, and Jordan Harrelson, Diane’s legacy lives on. Each of her sons carries forward her teachings and the strength she exemplified, embodying the essence of her character. Diane Lou Oswald’s story is a reminder of the profound impact a mother’s love and values can have, transcending time and financial measures to leave a lasting imprint on the world.

The Lasting Influence of Diane Lou Oswald in the Entertainment Industry

Diane Lou Oswald’s impact on the entertainment industry is deeply rooted in her influence on her son, Woody Harrelson’s, remarkable career. As a loving and supportive mother, she played a pivotal role in fostering Woody’s passion for performing from a young age. Her unwavering belief in his talent provided the foundation for his eventual success and celebrity status in Hollywood.

Beyond her role as a guiding force in Woody’s life, Diane made her mark in the entertainment world through her talents and accomplishments. As an accomplished actress and theater director, she showcased her dedication to the craft and left a lasting impression on audiences. Her contributions to the industry serve as a testament to her skills and passion for the arts, further enhancing her legacy in Hollywood.

Diane Lou Oswald’s influence extends far beyond her family relationships, inspiring aspiring actresses worldwide. Her son, Woody, carries on her legacy, transmitting her talent and passion to future generations. Diane’s impact on the entertainment industry is undeniable, and her name will be remembered and celebrated for years to come.

Diane Lou Oswald: Contemplating Her Philanthropic Work and Advocacy

Diane Lou Oswald’s philanthropic endeavors were not just acts of charity; they were a reflection of her deep-seated belief in making a meaningful difference in the world. She centered her charitable activities around the simple yet profound concept of giving back, leaving a lasting impact on both global issues and local communities. Through her kindness and generosity, Diane touched the lives of many, embodying the true essence of humanitarianism.

As a passionate advocate for various social causes, Diane used her voice and platform to raise awareness and drive change. Her dedication to environmental preservation, educational reform, and equal rights showcased her unwavering commitment to making the world a better place for all. Diane not only made financial contributions but also inspired others to join the fight for justice and equality, demonstrating the power of collective action in creating positive change.

Diane Lou Oswald’s legacy serves as a beacon of hope and inspiration, reminding us of the impact that one individual can have on the world. Her philanthropic work and advocacy efforts continue to inspire others to take action and contribute to a more just and equitable society. As we honor her memory, we remember the importance of showing compassion, and generosity, and tirelessly striving for a better world for future generations.

Facts About Diane Lou Oswald

  1. Diane Lou Oswald was born in 1937 in Lebanon, Warren, Ohio, and grew up in an upper-middle-class family.
  2. She worked as a legal secretary, showcasing meticulous attention to detail and organizational skills.
  3. Diane married Charles Harrelson in 1959 but separated in 1964, leaving her to raise their three sons alone.
  4. Despite her ex-husband’s criminal activities, including being a convicted contract killer, Diane never turned her children against their father.
  5. Diane’s parents were Kenneth and Mary Lou Oswald, with her father passing away in 1957.
  6. She had a strong influence on Woody Harrelson’s acting career, instilling in him a passion for the craft from a young age.
  7. Diane was involved in various charitable activities, demonstrating her commitment to giving back to communities.
  8. Her advocacy extended to environmental causes, educational reform, and equal rights, reflecting her passion for social change.
  9. Diane’s supportive notes to Woody during his career milestones highlighted their close and loving relationship.
  10. Woody attributes his work ethic and love for nature to the values Diane instilled in him, showcasing her enduring influence.


Diane Lou Oswald, born in 1937, was a remarkable woman known for her resilience, dedication, and influence. She began her professional journey as a legal secretary, where her meticulous attention to detail and organizational skills set her apart. Despite facing challenges in her personal life, including a tumultuous marriage to Charles Harrelson, Diane raised three sons, including Hollywood actor Woody Harrelson, as a single mother.

Diane’s impact extended beyond her role as a mother. She actively participated in charitable activities and advocacy efforts, focusing on causes such as environmental preservation, educational reform, and equal rights. Diane’s influence on Woody’s successful acting career was profound, as she nurtured his passion for performing and supported him through his achievements.

Throughout her life, Diane’s kindness, resilience, and dedication to making a positive impact left a lasting legacy. Her story serves as an inspiration, highlighting the importance of perseverance, compassion, and the enduring bond between a mother and her children.

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