The Oscar-winning movie Robert Redford hated making: “I became resentful”

Making movies is never easy, with hundreds of moving parts required to work in synchronicity during production to ensure shooting goes off without a hitch. It applies to every film, whether the end result is acclaimed or abhorred, but Robert Redford discovered during one of his most trophy-laden gigs that even his closest collaborators had the ability to get under his skin.

On the surface, reuniting one of Hollywood’s most prominent leading men with a director he’d worked with more than any other should have been the smoothest sailing. They were friends when the cameras weren’t rolling, knew each other’s approach to their craft inside out, and constantly worked together because they knew it would bring out their best.

Redford played one of his first major roles in a feature in 1965’s comedy This Property Is Condemned, which doubled as Sydney Pollack’s second stint behind the camera. Saying they hit it off might be an understatement, considering they’d make another six pictures together as director and star in a relationship that lasted until 1990s Havana.

In between those two points, the pair put their heads together and delivered smash hit period piece Jeremiah Johnson, romantic drama The Way We Were, politically charged thriller Three Days of the Condor, and the western dramedy The Electric Horseman. They always found their way back to each other every few years, but their penultimate movie wasn’t without its strain.

At first glance, re-teaming Redford and Pollack for the sixth time and adding Meryl Streep into the mix was about as close to a guarantee of success as anyone could find in Hollywood. Sure enough, that’s exactly what happened when 1985’s Out of Africa earned over a quarter of a billion dollars from cinemas, secured 11 Academy Award nominations and walked away with seven prizes, including ‘Best Picture’ and ‘Best Director’.

Despite their familiarity with each other, it sounds like there was a hint of jealousy during filming. Redford and Pollack were hardly strangers, but the filmmaker seemed to have his issues with his regular leading man and Streep getting along famously during their downtime and cutting him out of the loop. “It caused ripples,” the actor admitted to Michael Feeney Callan. “We liked to talk. We’d be off-camera, between takes, taking it easy.”

Redford shared that he and Streep “had a sense of humour in common,” which made shooting Out of Africa a particularly enjoyable experience until Pollack tried to thwart their bond. “Sydney didn’t like that,” he explained. “He would break it up. It bothered him that I was connecting with her in some way that didn’t fit his picture of me or of us as a team. That wasn’t easy to deal with because I felt I was in a vice, and I became resentful.”

They’d already made five movies together, but the sixth time didn’t mark the charm after Pollack fostered resentment in one of his most frequent on-camera regulars by trying to sabotage the friendship blossoming between Redford and Streep. It was playground behaviour on a Hollywood scale, which admittedly isn’t out of the ordinary based on how petty the business has always been.

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