Joshua Goldman
Joshua Goldman
min read · September 17, 2025 · Entertainment

The Enigmatic Legend: Robert Redford's Hollywood Cold War

Redford, who has died aged 89, never won an Oscar as an actor, in part because he refused to play the celebrity game of going to parties and hanging out with false friends. Pictured: Redford with Dustin Hoffman in All The President's Men

The Enigmatic Robert Redford: A Life of Contrasts and Controversy

The Hollywood legend has left us, but his legacy remains shrouded in mystery. Robert Redford's life was a paradox - a man who reveled in the spotlight yet despised its superficiality. His journey from a poor childhood to becoming one of the most iconic stars of our time is a tale of contradictions and controversies that will leave you wondering about the real person behind the persona.

Born in 1936, Robert Redford grew up with an absent father who was more interested in his Standard Oil job than his son's life. But it was his uncle David who played a significant role in shaping him - until his untimely death on the battlefield when Redford was just eight years old. His mother, Martha, tried to fill the void, teaching her young son to drive before he turned ten and instilling in him a love for Native American culture that would stay with him forever.

Redford with Mia Farrow in the 1974 box office hit The Great Gatsby

Redford's early life was marked by hardship and tragedy - his first wife, Lola Van Wagenen, gave birth to their baby son, Scott, who died in his tenth week. The heartbreak was compounded when Redford's mother passed away at 40 from complications related to a double stillbirth. His father remarried soon after, leaving Redford feeling abandoned and lost.

But acting became his lifeline - a way to escape the pain of his past and find identity. After enrolling in the American Academy of Dramatic Arts, he met Lola again and they eloped to Las Vegas on a shoestring budget. Their marriage lasted almost three decades, producing two more children besides Scott's younger brother James.

Redford's rise to fame was meteoric - from bit parts to leading roles, he conquered Hollywood with ease. But beneath the charming smile and iconic good looks lay a complex web of insecurities and contradictions. He had an 'inverted vanity' that made him self-conscious about his appearance, often insisting on being filmed from his left side to avoid drawing attention to his cluster of moles.

Redford with Barbra Streisand in the 1973 classic The Way We Were

He was a control freak who hated watching rushes - "Who am I kidding?" he'd exclaim at the screen. His perfectionism extended to every aspect of his life, including sports. He was an intimidating opponent on the ski slopes and tennis court, always pushing himself to win.

But Redford's greatest passion lay elsewhere - in the wilderness. He spent countless hours hiking and riding across America, often for weeks on end, to escape the trappings of fame. "There are no mirrors to tell you how your beard is, or if there's a boil on your nose," he'd say with a twinkle in his eye.

He was a man of strong convictions - refusing to compromise on his art or play the celebrity game. He turned down iconic roles like Dustin Hoffman's in The Graduate and Anne Bancroft's in Rosemary's Baby, not because he was afraid of failure but because they didn't resonate with him on a deeper level.

Redford with second wife Sibylle, who he met after his first marriage of 30 years ended

Redford's relationships were also marked by intensity - with co-stars like Jane Fonda and Meryl Streep, who shared his passion for authenticity. He was fiercely protective of his family and private life, often using his mountain retreat as a sanctuary from the prying eyes of the paparazzi.

In 1980, he made history directing Ordinary People, a film that would earn him an Oscar but still leave him feeling disconnected from the industry. His independent spirit led him to create the Sundance Film Festival in the 1980s, a haven for artists who rejected the commercialism of Hollywood.

Throughout his career, Redford remained enigmatic - a star who defied categorization. He was a romantic figure, a rebel with a cause, and a loner who preferred the solitude of the wilderness to the spotlight's glare. His final years saw him continue to push boundaries - starring in All Is Lost (2013) as a lone yachtsman fighting for survival.

The Hollywood icon with Paul Newman as Butch Cassidy in The Sundance Kid

In 2018, he announced his retirement from acting, citing the loss of privacy that came with fame. "Life is not about Boy Scout maxims," he said wistfully. "Life is about winning. To be loved, to be a nice guy, is not necessarily a goal."

And so Robert Redford leaves us, a legend in his own right - complex, multifaceted, and forever shrouded in mystery. His life was a paradox of contradictions - a man who reveled in the spotlight yet despised its superficiality. As Meryl Streep so eloquently put it: "One of the lions has passed."

Robert Redford during the filming of the 1975 movie Three Days of the Condor

Redford in a still from the 2015 film A Walk in the Woods

He founded the nonprofit Sundance Institute in 1981, which became a staple in the arts world for years to come

In 1984, he transformed a struggling film festival into what's now known as The Sundance Film Festival, in Park City, Utah

However, as the festival grew more and more popular over the years, Redford spoke out against the commercialization of the event

In 1969, Redford posed on the set of Butch Cassidy & The Sundance kid, above

He often starred alongside many of Hollywood's leading ladies at the time, like Barbra Streisand in The Way We Were in 1973, and Jane Fonda in the 1967 film, Barefoot in the Park, seen above

The actor began directing later in life and won an Oscar for Ordinary People in 1980, as he's seen here in A Bridge Too Far

In 2016, President Barack Obama awarded Redford as a recipient of the Presidential Medal of Freedom, which is America's highest civilian honor

Redford won multiple Golden Globe Awards, including Best Director for Ordinary People in 1981

In 2009, Redford married German artist Sibylle Szaggars, pictured above

In a 2024 interview with Orion Magazine, Redford shared his advice for young filmmakers who want to urge their viewers to care about something

Redford, pictured here with Margaret Mead and Lola Redford, recently urged young filmmakers to 'get involved,' and to not take it 'lightly'

In 1973, Redford and Barbra Streisand played romantic interests in hit film, The Way We Were