This 88-Year-Old Actor Lost 2 Sons, Though Got a 2nd Chance at Love with 2 Decades Younger Wife – His Story

Though he would go on to earn acclaim across decades in film and television, his early adult years were shaped more by survival than stardom. Before acting classes and iconic roles, he was a college dropout painting in Europe, then a newlywed scraping by in New York. It was there that his personal life began in earnest, marked by hardship as much as ambition.

Later, as his work took off, his private world remained full of quiet battles, from life-threatening illness in his family to traumatic losses that stretched over decades. Through it all, he continued to move forward, leaning into both his art and his responsibilities. And while relationships came and went, a chance meeting in the late 1990s would open the door to something lasting.

His career took shape across five decades, defined by roles in films that still carry weight today. He was part of the “Butch Cassidy and the Sundance Kid” cast in 1969, then “All the President’s Men” in 1976. In the 1980s, he starred in “The Natural” and directed “Ordinary People,” which went on to win multiple Oscars.

Throughout his career, the actor has always been reserved in interviews and careful about how much of himself he showed on screen. He became known for setting boundaries in ways that stood out even to his co-stars.

Jane Fonda, who acted opposite him in “Barefoot in the Park” and “The Electric Horseman,” once said, “He did not like to kiss. I never said anything [to him about it]. And he’s always in a bad mood, and I always thought it was my fault.” Still, she added, “He’s a very good person.”

His acting training came after an early interest in art. He was born on August 18, 1936, in Santa Monica and raised in Van Nuys, California. After high school, he received a baseball scholarship to the University of Colorado, but dropped out during his sophomore year.

The actor and producer later referred to himself as “the campus drunk” and said he left before anything could take shape. He spent a year in Europe afterward, focused on painting, before returning to Los Angeles. That return marked the beginning of the most formative chapter in his early life.

Living in an apartment building in L.A., he met Lola Van Wagenen, a 17-year-old bank teller. The two married in 1958 and moved to New York City shortly after. There, he enrolled at the Pratt Institute of Art and later pursued acting at the American Academy of Dramatic Arts.

A friend, stockbroker Collins, recalled meeting the couple during that time. “Even then, he had charisma,” said the friend. “People really noticed him.” He added, “I first met [him] and his wife when they were living on bouillon on Manhattan’s Upper East Side.” In the first year of their marriage, he and his wife faced a devastating loss.

Their five-month-old son died of sudden infant death syndrome in 1959, while they were still trying to build a life in New York. “That was a tough hit,” he said years later. “It was our first child. We were in New York, and we were broke. It was really tough.”

They were both still very young — he was 21, and she was 20 — and had only recently moved across the country to begin building a life together. He later spoke about how difficult it was to process what had happened at that age. “We had other children who came. But something like that doesn’t get completely dismissed,” he said.

Although he rarely spoke about the experience publicly, he raised money over the years to support research into the condition that took his son’s life. After the loss of their first child, the couple went on to have three more children: Shauna, David James — known as Jamie — and Amy.

The couple remained together for decades, sharing both the early struggles of his career and the private griefs that followed. Their marriage survived the death of their first child and the ongoing health battles of their son, Jamie. For many years, he kept his personal life guarded, and the end of the marriage was no exception.

He did not speak publicly about the divorce, saying only, “I got lost for a time.” Screenwriter Budd Schulberg once remarked that he had never expected the marriage to end. “He told me he was totally faithful to his wife… They were very tight; they went through a lot of stuff together.”

After the divorce, he had a brief romance with actress Sonia Braga in the late 1980s. He later entered a long-term relationship with costume designer Kathy O’Rear, which ended around 1995. The years that followed the divorce were not without hardship.

The couple’s son, Jamie, faced serious health problems for most of his life. He had lived with colitis for many years, which progressed to cirrhosis and eventually led to two liver transplants in the 1990s. He underwent one of the procedures in 1993.

At the time, his father was directing “Quiz Show” in New York, and flew out to Omaha every weekend to be by Jamie’s side at the hospital he and his family had chosen. When the first transplant proved unsuccessful, Jamie underwent a second procedure, which was followed by further complications.

“But now he’s fine,” his father said at the time. Jamie died in October 2020, at the age of 58. The cause was bile-duct cancer in his liver. At the time of Jamie’s death, a spokesperson for the family shared a brief statement. “The grief is immeasurable with the loss of a child,” she said.

“Jamie was a loving son, husband, and father. His legacy lives on through his children, art, filmmaking, and devoted passion to conservation and the environment,” she added. His father did not release a personal statement, but the spokesperson asked for the family’s privacy during what she described as a difficult time.

Shauna also went through a traumatic period in the mid-1980s. In 1983, her longtime boyfriend, Sidney Wells, was murdered. Just eight months later, she lost control of her Ford Bronco and crashed into the freezing Jordan River near Salt Lake City.

A local woman, Dorine Staker Rivers, dove into the icy water to help pull Shauna, semiconscious, out of the vehicle. Months later, Dorine met Shauna’s father, Robert Redford, at the premiere of “The Natural.”

She recalled him saying, “Saying thanks just isn’t enough,” and remembered how affected he seemed. “I believe he was at a loss for words. He was just being a dad at that point.”

In the late 1990s, Robert met Sibylle Szaggars, a German-born abstract and environmental artist. The two crossed paths at Sundance, where she had been active in the art community. Over time, their relationship deepened, and after more than a decade together, they married in 2009.

Sibylle, whose career spans nearly four decades, is known for work that blends environmental themes with performance art. Her projects have been exhibited across Europe, Asia, the United States, and South America. In 2013, she collaborated with Icelandic composer David Thor Jonsson.

Together, they launched “The Way of the Rain,” a staged art performance incorporating music, spoken word, dance, and visual art. During the COVID-19 pandemic, she and Robert began creating “The Way of the Rain – Reflections on Earth,” a video series produced in collaboration with composer Tim Janis.

The series was screened at events hosted by Earth X, National Geographic, and the United Nations, among others. He spoke briefly about their life together in a 2011 interview. “She’s a very special person,” he said. “She’s younger than I am, and European, which I like, so that’s a whole new life.”

On March 9, 2025, Robert appeared on screen for the first time in years. The cameo took place during the Season 3 premiere of “Dark Winds,” a television series set in the 1970s Southwest, which follows Navajo tribal police officers.

In the episode, Robert appears as a jailed man playing chess opposite author George R. R. Martin, who also makes a cameo. The scene had been in discussion since the show’s first season. Robert, who serves as an executive producer on the series, had considered appearing in the Season 2 finale but ultimately filmed the chess scene instead.

The moment was shot on a closed set, at Robert’s request. Director Chris Eyre said that the experience of directing Robert left a lasting impression. “Bob is so kind, and he was so nice on the day,” he shared, recalling the excitement of the crew. “You’re doing a scene with Robert Redford—that’s incredible.”

This appearance marked Robert’s first on-camera role since 2019’s “Avengers: Endgame,” where he briefly reprised his character from “Captain America: The Winter Soldier.”

In the years between, he lent his voice to the 2020 experimental film “Omniboat: A Fast Boat Fantasia,” HBO’s “White House Plumbers” in 2023, and his wife’s 2024 stage performance, “The Way of the Rain – Hope for Earth.”

Now 88, Robert has continued to stay active through his creative work and personal life. In addition to producing television and narrating multimedia projects, he remains involved in environmental advocacy, often alongside his wife, Sibylle.

He still rides horses, skis, and plays tennis, saying in one interview, “I still have energy. When that starts to shut down, I might start to think about age.” Back in 1998, Robert said he had four grandchildren — born to Jamie and Shauna — who referred to him as “Bo-Pa” or “Ba-Poo,” depending on which child was speaking.

“The word grandfather is weird,” he said at the time. “It feels like some old guy in a robe.” Though best known for his decades-spanning career in film and television, Robert has always placed a higher value on the role he played off-screen.

“People think it’s been easy for me,” he said. “The hardest thing in the world is when your children have problems.” Looking back, he described his greatest accomplishment in simple terms.

“I’ve made some interesting movies, and I’ve been very satisfied with the work, but if someone wrapped it all up and said to me, ‘What’s your greatest achievement?’ I’d say, ‘The children. They’re the best thing in my life,'” he stated.