The steamy ‘Havana’ scene Sydney Pollack had to push Robert Redford for
Becoming a sex symbol and heartthrob isn’t a status an actor intentionally seeks to attain when they break into the industry, but being a very handsome man didn’t exactly work against Robert Redford when he rose up the ranks in the 1960s.
Well, it did for a spell after he was denied the chance to play Dustin Hoffman’s Academy Award-winning role in The Graduate because he simply wasn’t believable as a character who struggled with women, and there was a time before he’d proven himself where the California native was brushed off by casting directors as little more than another pretty face.
The two key figures in shifting that perception were Sydney Pollack, who hired Redford for his first major dramatic leading role in 1966’s This Property Is Condemned to set the stage for a decades-spanning partnership, and Paul Newman, who insisted that he be cast as the other title character in Butch Cassidy and the Sundance Kid, the movie that launched him towards the top of the A-list.
Redford and Pollack would make another six pictures together, so it was clear there was friendship, trust, and mutual admiration there. That’s just as well because the filmmaker was probably one of the only auteurs in town who’d be able to convince the actor to shoot a scene he was dead against filming.
Their final feature as a pairing was 1990’s Havana, which flopped at the box office and took a pasting from critics. Pollack remained adamant that it was his most overlooked and unfairly treated film as a director, but it turns out that he had to convince Redford to shoot one of its steamiest moments.
The story follows the leading man’s hedonistic gambler Jack Weil as he enjoys a life of luxury in Cuba. However, when he runs into Lena Olin’s femme fatale and discovers she’s a communist sympathiser, he gets drawn into a world of danger and intrigue when he ends up imprisoned alongside her husband.
One scene required Redford to engage in a threesome, and initially, he wasn’t having it. “Well, that was a big part of that world,” Pollack told Box Office Mojo of why he decided the sultry tryst was necessary for his Cuban-set dramatic thriller. “Redford initially didn’t want to do the scene with the two girls, and I insisted because that’s the guy: the card-playing playboy. He picks up the two girls, and he sleeps with them.”
It was all in the service of character, even if Redford was hesitant to hop into bed with two women. However, if anyone was capable of twisting his arm and getting the star to do something he didn’t want to do, then there was nobody better placed than Pollack.
