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6 Career Defining Films Of Robert Redford

6 Career Defining Films Of Robert Redford

Robert Redford best movies

In the Toast series today, we celebrate Hollywood legend and Oscar-winning director Robert Redford, whose illustrious career spans six decades. The ‘Sundance’ kid turns a glorious 85 today!

Robert Redford once said in an interview that he loved mythology growing up. The mystical, powerful gods and goddesses. And the idea that we humans could somehow, if we’re very lucky, be gifted with their magical superpowers. Yes, you know where this is going.  

The actor. The Oscar-winning director. The Father of Independent Film (aka the Sundance Institute and its offshoots). The environmentalist. The social activist. The notoriously private man off-screen. And yes, that rare, rare Hollywood star who was actually born in Los Angeles. (He is to Los Angeles what Al Pacino and Robert De Niro might symbolize to New York City. Redford has that carefree blonde West Coast charisma, as opposed to Pacino and De Niro’s delightfully tough New York City street manner and dark locks.)     

All told, Robert Redford is a Hollywood god. He’s had a beyond successful career spanning the 1950s to just a few short years ago, before he casually hung up his boots (retiring as an actor at least!) in his trademark pleasant, understated manner. Asked personally by icon Natalie Wood to appear in her 1965 film, Inside Daisy Clover, he has never looked back.  

He’s starred in sweet flicks like Barefoot in the Park (1967) and smash hits like Butch Cassidy and the Sundance Kid (1969). There are also smaller films like Downhill Racer (1969) and Jeremiah Johnson (1972) that inspired him to one day start Sundance – and to pioneer the feasibility of an independent film movement that could co-exist harmoniously alongside a commercially-driven Hollywood mainstream market. Redford achieved all this, and before 50!


Oscar For Lifetime Achievement 

Since the 1970s, he’s also become a directorial force, making thoughtful, compelling films like Ordinary People (1980), which won multiple Oscars including Best Director and Best Picture. He also directed A River Runs Through It (1992), notable for its young breakout star of Brad Pitt, and Quiz Show (1994), among others. No surprise, in 2002, Redford was gifted with an honorary Oscar for Lifetime Achievement.  

Born and bred in Los Angeles, but choosing the vast, beautiful mountainous American West as his inspiration-filled home in adulthood (Utah, New Mexico, etc.), Redford is a beloved enigma who’s left an indelible footprint in the film industries of the world. He’s both a Hollywood and global treasure.  

What’s more, after all these years, people are still intrigued by him, want to know him, are intimidated by him, and are enamored by him. So this August 18, 2021, here’s wishing a happy, heartfelt 85th birthday to Robert Redford, a true friend to film. Thank you, Robert Redford, for your unique, pioneering, and talented spirit. Now what great movies have defined this phenom’s career? Let’s get down to it.


6 Career-Defining Films of Robert Redford 

1. Butch Cassidy And the Sundance Kid (1969)

Usher in the ultimate Dynamic Duo of New Hollywood, Paul Newman and Robert Redford. Or in millennial terms, the ultimate Bro-mance. Matt Damon and Ben Affleck? Tobey Maguire and Leonard DiCaprio? All great, but let’s hail the original. Filmed in the late 1960s, when Hollywood was reinventing itself to be more realistic and gritty, this Western masterpiece is a fresh take on an old genre. There’s witty banter, some modern Burt Bacharach music, and it’s a ‘buddy film’ that makes early 1900s outlaw train robbers (Butch and Sundance) somehow likeable anti-heroes. Redford was relatively new to movies, and this film catapulted him to super-stardom. It also forged a lasting off-screen friendship between Redford and Newman. They also teamed up again for 1973’s super-successful The Sting. What an awesome Hollywood friendship.


2. The Way We Were (1973)

Call him leading man, heartthrob, the hottest male superstar on the planet. This movie solidified all that. Say what you want about the questionable moral goodness of his character, Hubbell Gardiner, but one can’t deny that Redford delivered his character well. He and fellow superstar Barbra Streisand (in one of her most career-defining roles ever), create on-screen chemistry that is palpable, dynamite, legendary. The list of adjectives goes on. In fact, The Way We Were has achieved such ‘romance’ icon status that it’s listed as a monumental #6 out of 100 for the AFI’s “100 Years… 100 Passions” romance movie ranking compiled in 1999.

At face value, it’s the quintessential ‘opposites attract’ love story. But, Redford and Streisand, the stunning 1970s superstars that they were, took that storyline and made it ‘next level.’ Wait, how’d they do that? Call it raw talent. Redford wisely knew how to play understated frat jock Hubbell to Streisand’s outspoken political activist Katie. Then add in legendary director Sydney Pollack’s dreamy filmmaking style, and this tearjerker romance rips your tender heart out, leaving you mournfully singing Barbra’s Streisand’s theme song, “Mem’ries, light the corners of my mind.” No surprise Redford was a hot commodity for romance films after this. Think Out of Africa (1985) and Indecent Proposal (1993) and Up Close and Personal (1996). There’s nothing like a Robert Redford romance.


3. All The President’s Men (1976)

Let’s be 1970s real. This movie had some potent 1970s Hollywood glitter showering down on it. Released in the USA’s Bicentennial year of 1976, and chronicling the fall from grace of recent real-life American President Nixon, All The President’s Men was the right movie at the right time. But for all the unfortunate, wrong reasons. Redford plays Bob Woodward alongside Dustin Hoffman’s Carl Bernstein, two real-life journalists investigating then-President Nixon and his suspicious connection to illegal activities at Washington, D.C.’s, Watergate Hotel.

This film is one of the best political movies ever, told without a lot of pomp and circumstance (it has that gritty, realistic, almost documentary 1970s vibe), and Redford and Hoffman’s performances are stellar. Redford was known for having a strong social conscious off-screen, and this movie was a perfect vehicle for him to explore questions related to politics and journalism, ethics and privacy. Redford shines. Definitely a must-see.


4. Ordinary People (1980)

Enter Robert Redford, Oscar-winning director. In fact, Ordinary People is a winner of four Oscars – Best Director, Best Adapted Screenplay, Best Supporting Actor for Timothy Hutton, and most importantly, Best Picture. It’s Redford’s beyond auspicious directorial debut. A tale about an upper-middle class family in the Chicago suburbs who experiences severe emotional trauma (the oldest son accidentally drowns in a boating accident, and the younger son becomes suicidal after surviving the accident), Ordinary People is beautiful in its subtlety, realism, and heart.

Redford shows us so much by way of his story selection, casting choices, cinematography style, etc. The result? You’re intrigued, mesmerized, and ultimately heartbroken. He taps into male sadness, then female strength (or stubbornness)? He shows us that “we” as so-called “ordinary people” are anything but. This movie is spellbinding in its own “ordinary” way. It’s pure magic, and told with a compassionate hand. Unsurprisingly, Redford went on to direct more amazing films after this exquisite debut. 

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5. The Natural (1984)

Here’s where Robert Redford channels his inner god and love for mythology. Flashback to him as a kid loving all those old mythology books, and we see why Redford wanted to star in The Natural. Quite simply, he’s a ‘natural’ fit. He plays Roy Hobbs, a baseball player with a lot of potential, due possibly to a magical bat made from the wood of a tree that gets hit by lightning. What’s more, this wood is from the tree next to where his beloved father died. See all the twists and turns, and if Hobbs makes it to the “pros.”

The Natural is epic, and touching, and a must-see for any sports fan. Redford successfully creates his mythical, mystical Baseball God. This movie undoubtedly inspired Redford to direct 2000’s The Legend of Bagger Vance, a film that explores the sport of golf in a mythical, mystical way.


6.  The Horse Whisperer (1998)

A culmination of everything Robert Redford is about, it’s Redford’s ultimate mash-up. Here’s why. It’s set in the American West. It’s a romance. It has political/social undertones regarding urban vs. rural lifestyles. Fourthly, Redford directs, and he showcases his trademark subtle, understated touches. Finally, his character, Tom Booker, is the namesake Horse Whisperer – a man with a supernatural ability to understand horses. Cue that mythological god status! The Horse Whisperer is visually gorgeous, the acting is excellent, and this film reminds us that movies can take their time.

It’s a millennial-era movie from 1998, and it seems to purposefully ask its viewers to slow down, take a seat, and simply watch a story unfold. After forty years in Hollywood showbiz, Redford had earned the right to make any picture he wanted. This movie is Redford at arguably his best, and he even directs a young Scarlett Johansson in one of her very first superb performances. (She’s pre-Black Widow head liner by a few decades.) A consummate giver to film, Redford galloped his way into the new millennium strong and full of sunshine. And lucky for us, this Sundance Kid is still radiating sunshine today. For the equestrian fans, here are 12 horse movies you’ll love.


Catch all the features from The Toast series here.


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