The Legendary Hollywood Antics Of Robert Redford
(Photo by Steve Schapiro)
โ€” 17 September 2025

The Legendary Hollywood Antics Of Robert Redford

โ€” 17 September 2025
Garry Lu
WORDS BY
Garry Lu

Nobody encapsulates the sentiment that โ€œthey donโ€™t make โ€™em like they used toโ€ more perfectly than the late great Robert Redford.

The veteran leading man effectively drafted the career blueprint that would be followed by Hollywood multi-hyphenates like George Clooney, Brad Pitt, and yes, Tom Cruise.

But Redfordโ€™s outsized legacy, while largely tied to his magnetic screen presence and rugged All-American good looks, extended beyond his equally outsized filmography, which spans classics from The Way We Were, 1974โ€™s The Great Gatsby, Three Days of the Condor, and All the Presidentโ€™s Men, to Out of Africa, Sneakers, Indecent Proposal, and Spy Game.

So much so that his impressive array of career accolades โ€“ an Academy Award for Best Director (Ordinary People), a quintet of Golden Globes, a sole BAFTA for Butch Cassidy and the Sundance Kid, and to a certain extent, his Presidential Medal of Freedom โ€“ is something of an afterthought compared to the vibrant mosaic of his total existence.

The man wasnโ€™t just a champion of the arts, lending his star power to elevate independent creatives, but a champion for worthy causes back when it was neither fashionable nor attached to social capital: environmentalism, indigenous rights, and LGBT rightsโ€ฆ These were key pillars of his principles that he wore on his sleeve. Not hashtags and headlines to curry favour with the public.

Hereโ€™s to the life well-lived of Robert Redford: Hollywoodโ€™s golden boy turned elder statesman.

RELATED: The Outrageous Billionaire Antics Of Kerry Packer


The Ultimate Charmer

To say Robert Redford quite enjoyed the company of ladies would be comparable to calling Sydney house prices โ€œa little pricey.โ€

He was, of course, among the earliest crop of post-Marlon Brando leading men considered genuinely beautiful by modern standards, and practically left a trail of swooning starlets in his wake.

Naturally, it wasnโ€™t uncommon for co-stars like Barbra Streisand (The Way We Were), Jane Fonda (Barefoot in the Park), Meryl Streep (Out of Africa), even Demi Moore (Indecent Proposal) and Michelle Pfeiffer (Up Close & Personal), to become โ€œinfatuatedโ€ with him over the course of their professional collaboration.

Even if they were already married, as was the case with Ms Fonda.

Success with the fairer sex was so ingrained within his DNA, in fact, that it disqualified him from fronting Mike Nicholsโ€™ The Graduate (the role famously went to Dustin Hoffman), despite having just worked together on a Broadway production of Barefoot in the Park.

โ€œI said, โ€˜You canโ€™t play it. You can never play a loser.โ€™ And Redford said, โ€˜What do you mean? Of course I can play a loser.โ€™ And I said, โ€˜Okay, have you ever struck out with a girl?โ€™ and he said, โ€˜What do you mean?โ€™ And he wasnโ€™t joking,โ€ said the director (via Vanity Fair).

โ€œIt was as if he couldnโ€™t fathom going to a restaurant and not ordering a meal.โ€

Ordinary women were no less immune. On the set of Peter Yatesโ€™ The Hot Rock, screenwriter William Goldman โ€“ who also penned other Redford pictures such as Butch Cassidy and the Sundance Kid, The Great Waldo Pepper, and All the Presidentโ€™s Men โ€“ recalled being blindsided by unsolicited comments made by an extra.

โ€œโ€˜My wife would like to f**k him.โ€™ This remark caught me more or less by surprise, and I turned to look at the guard: ordinary-seeming guy, maybe 40, in his prison uniform,โ€ recounted Goldman.

โ€œโ€˜I mean, you donโ€™t know what she would give just to f**k himโ€ฆ She said to me today, my wife, that she would get down on her hands and knees and crawl just for the chance to f**k him one time. One time.'โ€

Was this the unofficial inspiration behind Indecent Proposal?

The cherry on top: during the making of The Way They Were, Robert Redford reportedly refused to perform the line, โ€œIt will be better this time,โ€ for his sex scene with Barbra Streisand.

โ€œRedford was never bad in bed, and so his character could never be either,โ€ author Robert Hofler explained in his book, The Way They Were: How Epic Battles & Bruised Egos Brought a Classic Hollywood Love Story to the Screen.

Itโ€™s also worth noting that very same scene, Redford took it upon himself to wear two sets of jock straps to contain his manhood.


A Bromance For The Ages

Butch Cassidy and the Sundance Kid didnโ€™t just catapult Robert Redford to a new stratosphere of mainstream fame. It also gifted him a true and lasting friendship with Paul Newman that was built on the foundation of mutual admiration and shared experience.

โ€œIt was just that connection of playing those characters and the fun of it that really began the relationship,โ€ Redford told ABC when Newman passed away from lung cancer back in 2008. 

โ€œAnd then once the film started, once we went forward, we then discovered other similarities that just multiplied over time, a common ground that we both had between us, interests and so forth, and differences.โ€

As per CNN, they were both devoted family men who, at one point, lived only a mile apart from each other in Connecticut; both leaned into philanthropy (โ€œRedford focusing on the environment and independent filmmaking, and Newman on founding charitable food company Newmanโ€™s Ownโ€); and like all the greatest bromances, they didnโ€™t take themselves too seriously.

In January 1975, Redford sent Newman an unusual gift for his 50th birthday.

Newman, a prolific petrolhead, had apparently fallen in love with Redfordโ€™s Porsche 904. But all the car talk had started to annoy Redford.

โ€œI started to get bored, because every time we got together all he talked about was racing and cars,โ€ he recalled in an interview at the John F. Kennedy Presidential Library circa 2014.

(Photo by Lawrence Schiller)

โ€œSo I decided to play a joke on him. I called a towing service and said, โ€˜Do you have any crushed automobiles? Do you have a Porsche?โ€™โ€

As it so happened, they did have a freshly totalled Porsche in stock. Like any good humoured mate would do, Redford gift-wrapped the wreckage, tied it up with a bow, and had it delivered directly to Newmanโ€™s doorstep in Connecticut.

For weeks, there was radio silence. Until a giant wooden box turned up in Redfordโ€™s lobby. After crowbarring it open, he found the remnants of the Porsche had been crushed even further into a cube. Redford then decided to undertake some next-level one-upsmanship by commissioning a sculptor to transform the debris into a garden ornament and had it placed in Newmanโ€™s lawn.

โ€œNeither Paul nor I ever spoke about it,โ€ he chuckled.

On another occasion, Robert Redford attempted to use Paul Newman as a reference while applying for an apartment in New York, to which the latter wrote:

To whom it may concern, Mr Robert Redford has owed me 120 bucks for over three years. He will not assume his obligation under threat of loss of friendship, honour, loyalty. I cannot in good conscience recommend him for anything.

In the weeks leading up to Newmanโ€™s death, Redford received a more sincere letter from his longtime amigo, which touchingly closed with: โ€œYou were the Sundance to my Cassidy โ€” always.โ€

(Photo by Lawrence Schiller)

RELATED: The Playboy Antics Of Jack Nicholson You Didnโ€™t Know About


As Stylish As They Come

This entire section could honestly be its own series.

The man The New York Times has described as โ€œan intellectual Marlboro Man tuned to maximum Americanaโ€ will, for decades to come, remain a Pinterest board #menswear fixture. As so eloquently outlined by Derek Guy, his passing โ€“ along with that of Paul Newman, Sean Connery, and Sidney Poitier โ€“ signals the gradual disappearance of a โ€œcertain type of 20th-century figure: men who embodied classic style, reflecting their taste, rather than a professional stylist.โ€

Suffice it to say, there are far more qualified sources of commentary for Robert Redfordโ€™s enduring status as a style icon than yours truly, so weโ€™ll just leave you with an assorted gallery of his finest on and off-screen looks.


More Than A Handsome Face (The Man Who Redrew The Map Of Cinema)

In an ecosystem as much-maligned as Hollywood โ€“ where backstabbing, subterfuge, and deception arenโ€™t simply the norm, theyโ€™re encouraged avenues for success โ€“ Robert Redford had a well-documented history of leveraging his clout to hold the metaphorical door open for whoever needed it.

If his screen presence defined an era, his work behind the camera and, more significantly, behind the scenes would go on to shape what came after it. Redfordโ€™s founding of the Sundance Institute in Park City, Utah circa 1981 (obviously named after his Butch Cassidy character) marked a decisive shift away from the entrenched and hegemonic machinery of Hollywood, and towards a more personal, risk-tolerant kind of filmmaking.

It began with mentorship and development labs, and eventually grew to establish the renowned Sundance Film Festival โ€“ both a legitimate platform for filmmakers working outside the studio system and a cultural barometer for the direction of cinema itself. The happy consequence was immediate and enduring.

Directors such as Steven Soderbergh, Quentin Tarantino, Darren Aronofsky, and even more notably, Ryan Coogler (Creed, Black Panther, Sinners) all trace their early breaks to Sundance. Independent film, once treated as a fringe concern, began to exert an actual gravitational pull on the wider industry, which is why we can have indie power players like A24 in the game these days.

โ€œNothingโ€™s more enjoyable to me than having created something you hope would create opportunities for other people to keep something alive,โ€ Robert Redford told Vanity Fair back in 2016.

โ€œWhen the mainstream starts to tighten up and put its forks into what it thinks is going to make money, things get narrowed down, and you miss some of the more experimental films.โ€

He continued: โ€œFor me, when people come into that new category โ€“ actors, directors, whoever โ€“ and something hits, I canโ€™t tell you how thrilling that is. When I see someone like Ryan Coogler with Fruitvale Stationโ€ฆ That was developed in our lab.โ€

โ€œIt went through three, four different directions with the script. It was hard work. To see that, to see documentaries come through, to see Liz Garbus come through, to see these people grow and achieve, to me thatโ€™s thrilling. Thatโ€™s my reward, it really is.โ€

Crucially, Sundance shifted the conversation around what cinema could look like and who it could belong to. It opened space for stories that were geographically, culturally, and emotionally distant from the nucleus of Hollywood โ€“ as we learned this week from 15-year-old Adolescence star Owen Cooper and his record-breaking Primetime Emmy win, you can find brilliance outside of all the usual money factories and cool kids clubs.

Both Redford and Sundance as a whole accelerated the normalisation of the idea that a film could be modest in budget yet expansive in ambition, and that creative risk could be rewarded on its own terms.

โ€œThe glory of art is that it can not only survive change, it can lead it.โ€

Fittingly, Robert Redford passed away peacefully in his sleep at Utahโ€™s Sundance Mountain Resort. It was as if the 89-year-old decided to finally enjoy some well-earned rest after decades of fighting the good fight.

Robert Redford poses for a picture at the Sundance Film Festival January 21, 1994 in Salt Lake City, Utah. (Photo by Tom Smart/Liaison)

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Garry Lu
WORDS by
After stretching his legs with companies such as The Motley Fool and the odd marketing agency, Garry joined Boss Hunting in 2019 as a fully-fledged Content Specialist. In 2021, he was promoted to News Editor. Garry proudly retains a blue belt in Brazilian Jiu-Jitsu, black bruises from Muay Thai, as well as a black belt in all things pop culture. Drop him a line at [email protected]

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