Robert Redford has passed away, but his work as a filmmaker will live on forever. Here are seven of his films that we feel are essential viewing to any fan of the man and his work. We’ll include a mix of universally beloved films and overlooked gems that are worth a second look.
Butch Cassidy and the Sundance Kid (1969)
The year 1969 changed what the public perception of the Western genre. While classics like Duel in the Sun, The Searchers, and High Noon challenged genre conventions and societal norms, it was the triple feature of True Grit, The Wild Bunch, and Butch Cassidy and the Sundance Kid that deconstructed the genre and dragged it into a whole new era.
Robert Redford and Paul Newman are a match made in heaven, a beautiful blend of masculinity, desperation, and bromance. They star as fictionalized versions of the real-life Butch and Sundance, who are already aware of their growing legend and celebrity, even as they lived on the criminal edge. With its mix of humor and drama, anchored by incredible performances from its leads and some innovative and breathtaking action sequences, this is the movie that turned Redford into a bona fide movie star.
There was an ill-advised prequel with none of the original cast, but if you want a true spiritual successor to Butch Cassidy and the Sundance Kid, check out 1973’s The Sting, which reunited Newman, Redford, and director George Roy Hill for another period piece about two affable criminals trying to stay one step ahead of the inevitable.
Jeremiah Johnson (1972)
Co-written by the great John Milius, Jeremiah Johnson follows its title character on his odyssey from a jaded military veteran to veritable mountain man. The film was shot on location throughout Utah, and it’s a stunning depiction of gorgeous American landscapes.
Redford carries the movie on his shoulders, going through unimaginable hardship on his endless journey to ‘get away from it all,’ or at least find something worth living for. It’s this bizarre mix of nostalgic whimsy and violent tragedy, and a career milestone for both Milius and Redford, as well as director Sydney Pollack, who would collaborate with Redford on more movies to come, including the next two entries on this list.
The Way We Were (1973)
Romantic movies are a dime a dozen, but a truly special love story only comes around every once in a while, in real life or otherwise. Take, for instance, The Way We Were. These days, the film might be less remembered than its iconic and often-covered theme song, which is a shame, since the movie still holds up as a masterful showcase for the acting talents of Redford and his co-star, Barbara Streisand.
Redford and Streisand play college students who strike up an unlikely romance. Redford plays an old-fashioned WASP, while Streisand is a leftist activist. Opposites attract, and the romance just about writes itself. Despite what its schmaltzy theme song might have you believe, The Way We Were is anything but. It’s a brutally honest depiction of two people with lives that get in the way of their love, or maybe it’s the other way around.
Three Days of the Condor (1975)
In the wake of the Watergate scandal that effectively brought down the Nixon White House, not to mention the hippie movement and the Kent State shooting, there was a spike of movies about distrust in the government and the ruthlessness of the powers-that-be to maintain their iron grip on power.
Redford stars as a CIA analyst who gets pulled into a paranoid conspiracy and forced to go on the run for his life while trying to uncover the truth of just what the heck is happening to him. Faye Dunaway, Cliff Robertson, and Max Von Sydow co-star. The film was hugely influential, to the point where Redford’s later role in 2014’s Captain America: The Winter Soldier was partly a tribute to his role in this film. It’s also a personal favorite of Claire Connors, the host of on-again-off-again podcast Under the Covers.
The Horse Whisperer (1998)
This list could consist entirely of movies from Redford’s 1970s heyday, but for the sake of mixing it up, let’s jump ahead to 1998’s The Horse Whisperer. This marked the first directorial effort by Redford in which he also starred. His co-star was a young child actress named Scarlett Johansson, who would grow up to be a superstar in her own right (and would reunite with Redford in the aforementioned Captain America movie)
Despite clocking in at nearly three hours in length, The Horse Whisperer is, to this day, a beloved family classic. Horses are majestic creatures that appeal to viewers of all ages, and the complicated human drama is especially compelling, if less salacious than what’s depicted in the original novel by Nicholas Evans. By this point in his career, Redford was a master of his craft, and as both an actor and director, The Horse Whisperer was not only the culmination of his career thus far, but an opening salvo for Scarlett Johansson, who would become one of her generation’s finest performers. Speaking of which, Johnansson’s directorial debut, the upcoming Eleanor the Great, is partly inspired by her experience working with Redford on this film.
The Last Castle (2001)
If there’s a wildcard on this list, it’s this one, but bear with me. The Last Castle was dismissed by critics and ignored by audiences, going down in history as a box office bomb. James Gandolfini, in the midst of his game-changing run on The Sopranos, was seen as miscast by those who had already typecast him as a tough guy “alpha male.”
In hindsight, though, The Last Castle is a forgotten classic. Redford stars as a disgraced general sent to a military prison run by Gandolfini’s corrupt warden. It’s not long before the two men come into conflict, ultimately escalating into an all-out civil war, with the flawed prisoners (Mark Ruffalo, Clifton Collins Jr, etc) serving as his army in one last battle in pursuit of the dignity they deserve.
Redford and Gandolfini are wonderfully cast opposite one another. Throughout his career, Redford has at once represented anti-authority while simultaneously having the gravitas of an authority figure himself, which makes his role in The Last Castle such a natural fit. Meanwhile, Gandolfini shines as a powder keg of impotent rage who demands, rather than commands, his authority.
The Old Man and the Gun (2018)
While not Redford’s last feature film role (that honor goes to his cameo appearance in Avengers: Endgame), 2018’s The Old Man and the Gun was Redford’s final role as a leading man. Nearly fifty years after he played a bank robber in Butch Cassidy and the Sundance Kid, Redford’s career came full circle.
He plays Forrest Tucker, a real-life bank robber who spent most of his days living life to the fullest… By robbing banks and breaking out of prisons, always managing to emerge one step ahead of the consequences while committing largely victimless crimes.
One can see The Old Man and the Gun as a capstone to Redford’s career, but I prefer to look at it as a coda, a post-credits adventure about how, even near the end of a life well-lived, the righteous never lose their spark. For a more traditional “capstone,” I recommend 2017’s Our Souls at Night, which reunited Redford with frequent co-star Jane Fonda, with whom he had previously acted in The Chase, Barefoot in the Park, and The Electric Horseman, all of which are absolutely worth watching… But that’s the thing about Robert Redford movies. Sure, his canon had its ups and downs, but Redford is one of those actors where, no matter what movie you pick, you’re going to have a good time.
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