There's a big cliché in Hollywood: if an actor gets big enough, he or she eventually wants to direct.
Sometimes this can be terrific. Clint Eastwood, for instance, or Kevin Costner. Other times…well, we're not going to talk about the William Shatner Star Trek movie. But in most cases, those actors were big stars before stepping behind the director's lens. That gave them the clout to walk into the office of the big-wigs and say, "I want do the next one."
That wasn't how Sydney Pollack did it.
Pollack was studying acting and wanted to be an actor, but when he came to Hollywood in the 1950s, something much different happened. His pal John Frankenheimer (another guy who went on to big things), asked him to help out with a movie he was doing featuring a lot of little kids. It was called The Young Savages, and it starred screen icon Burt Lancaster. Lancaster told Pollack that he could do great things behind the camera if he wanted to.
Pollack took the colossal movie star's advice. He started with television, which was big and booming in the early 1960s, and which gave him plenty of room to learn how to make a story work. His training as an actor meant he could work very well with other actors. After cutting his teeth on shows like The Fugitive and Alfred Hitchcock Presents, he was ready to move to the big screen.
He first effort, The Slender Thread (1965), didn't exactly set the world on fire, but it was a start. Pollack was nothing if not a diligent worker. Four years later, he scored a big hit with They Shoot Horses, Don't They? about a dance marathon that goes wildly wrong. The film made a tidy profit and scored nine Oscar nominations that year, including one for Pollack.
His next film was a western called Jeremiah Johnson (1972)—another hit—which marked the second time he worked with Super Mega Drop-Dead Gorgeous Star Robert Redford. (The first was another snoozer called The Property is Condemned, which is content to sit ignored at the bottom of the Netflix queue).
Pollack and Redford clearly got along like a burning house, which is probably why they started working together a lot. Like a super lot. They made seven films together in all, and Out of Africa was number six.
The sixth time was the real charm, apparently, since Out of Africa nabbed Pollack two Oscars for directing and producing (that big Best Picture prize was his). Of course, by then, he was a regular staple at the Oscars, not only for his movies with Redford, but also for the likes of Tootsie and Absence of Malice.
Pollack took time to act, too, sometimes in his own movies (check out his very funny scene with Dustin Hoffman in Tootsie) and sometimes in others (he showed up with bells on to act for Stanley Kubrick in Eyes Wide Shut). His Tootsie gig came because Dustin Hoffman was so tired of arguing with Pollack about his character that he suggested he play the character's argumentative talent agent.
What's that about art imitating life?
Pollack was known for being able to deliver direction in a supportive way (the above incident being a noticeable exception), but he was a perfectionist for sure. Redford said about him:
I don't mean to call him a control freak, but there's no one more interested in control than Sydney. He's a careful person, he cares about how he's thought of, and he doesn't take chances. (Source)
Streep saw Pollack as a constant worrier, and Pollack agreed. He thought that's what drew him to make movies about unsolvable problems. He didn't like 100% happy endings, because life isn't like that. In obsessing and worrying about every aspect of a story, he'd eventually realize that many arguments, like many people, just can't be reconciled.
What happens with me is that I get interested in a film as an argument between two points of view, so that the picture becomes a way of giving both sides equal weight. And sometimes I wind up digging a ditch between the two people that's so wide it seems false to try to reconcile them. Besides, I sense something that's true or satisfying in the separation. (Source)
Out of Africa was a high water mark for Pollack. He made another terrific film with the Tom Cruise legal thriller The Firm. His later movies tended to be smaller, independent films with his own production company, Mirage Enterprises. For those films, he worked without high-wattage stars that were his bread and butter for most of his career.
Pollack died in 2008 at the age of 73. But like any great artist, even death didn't stop him. In 2008, he got a posthumous Best Picture Oscar nomination for his producing role in The Reader.
Not bad for a guy who thought he'd spend his life on the other side of the camera.