A look back at the late director's work with Hollywood A-listers like Robert Redford and Dustin Hoffman

Lately, young filmmakers seem to be obsessed with the movies of the ’70s. Which is to say, the movies of Sydney Pollack. In that revolutionary decade, there were thornier mavericks behind the camera (Robert Altman and Francis Ford Coppola come to mind) and bigger titans at the box office (Steven Spielberg and George Lucas), but Pollack was the director that actors of that era trusted the most. Al Pacino, Jane Fonda, Paul Newman, Faye Dunaway, Dustin Hoffman, and Meryl Streep all lined up to work for the Academy Award winner. Maybe it was his knack for leading so many of them to Oscar nominations (a dozen, to be exact). Or maybe it was because he began his own career as an actor and seemed to get them. Either way, Pollack’s gift was bringing out the best in his stars. And on May 26, they lost their biggest champion when Pollack, 73, died of cancer at his home in Los Angeles.

As a teen in South Bend, Ind., Pollack was torn between becoming a dentist (his father’s wish) and pursuing acting. Choosing a life on the stage, he set out for New York City in the early ’50s, skipping college and enrolling at the Neighborhood Playhouse, where he studied under legendary drama coach Sanford Meisner. Pollack soon landed a string of bit parts on Broadway and TV, but his lack of leading-man looks — tall and lean as a beanpole, with a thicket of wiry curls atop his head — did his career no favors.

During filming of his big-screen debut in 1962’s War Hunt, the frustrated Pollack met another hungry young actor — an impossibly handsome blond named Robert Redford — who became a lifelong friend and collaborator. On the advice of Burt Lancaster, Pollack found steadier work behind the camera. And like so many of the best directors of his era (Sidney Lumet, John Frankenheimer), Pollack honed his craft on TV melodramas like The Alfred Hitchcock Hour and Kraft Suspense Theatre.

In 1965, Pollack helmed his first feature, The Slender Thread, lucking into a cast that included Sidney Poitier and Anne Bancroft. ”I was just a kid,” Pollack told EW in 2005, ”and I started out as a spoiled brat by having two Academy Award winners in my first film.” He also dismissed the finished product: ”You have to take Dramamine to watch that movie because the camera is so busy. I was just trying too hard.”

The next year, Pollack cast his pal Redford in an adaptation of Tennessee Williams’ This Property Is Condemned. The film wasn’t anything special, but the chemistry between the tow-headed WASP and the Brillo-haired Midwesterner was. Pollack and Redford reteamed six more times, most famously in a pair of very different box office hits from the ’70s. Pollack’s bittersweet 1973 love story The Way We Were remains the three-hankie standard for any movie where two mismatched souls fall in love. And his 1975 conspiracy thriller Three Days of the Condor is a harrowing and twisty slice of post-Watergate paranoia that became embedded in the DNA of such recent films as Syriana and Michael Clayton, the latter of which featured Pollack as both a costar and producer.

Together, Redford and Pollack made films that ran the gamut from well-meaning misfires (1990’s Havana and 1979’s The Electric Horseman) to criminally underrated epics (1972’s Jeremiah Johnson) to elegant and stately Academy Award winners (1985’s Best Picture and Best Director winner, Out of Africa).

It’s particularly telling that over the course of his five-decade career, several actors who received nominations in Pollack’s films — such as Melinda Dillon and Teri Garr — were never nominated again. He had the Midas touch. He could tease out great performances, showing off his actors in the most flattering light like diamonds in a jewelry shop window. But it was tension rather than trust that produced what is arguably Pollack’s most indelible (and certainly funniest) movie, 1982’s Tootsie. By all accounts, Pollack and his star, Dustin Hoffman, fought like wildcats. But the result was pure magic, highlighted by Pollack’s wonderful turn as Hoffman’s flummoxed agent. Tootsie earned $177 million at the box office and snagged 10 Oscar nominations — a rare feat for a comedy.

Less publicized was Pollack’s work as a Hollywood producer with more than 40 credits to his name. During the last decade of his life, he became an elder statesman, mentoring the likes of his producing partner Anthony Minghella (Cold Mountain), who died unexpectedly a couple months ago, and George Clooney. Along with producing Clooney’s Michael Clayton, Pollack played the bullying head of an amoral law firm. It was one of his last onscreen appearances, and the character couldn’t have been further from the man playing him. ”Sydney made the world a little better, movies a little better, and even dinner a little better,” said Clooney in a statement. ”He’ll be missed terribly.”

Ironically, it was this type of supporting turn that made Pollack a familiar face to mainstream viewers. No matter how small the role, his acting always seemed effortless, lived-in. Pollack could play for belly laughs (as Will’s well-intentioned dad on Will & Grace) and plumb darker depths as well (as a doctor imprisoned for murder in the final season of The Sopranos). ”He was an incredible director, but also a great actor, even though he never wanted to take credit for it,” says Will & Grace‘s Eric McCormack. ”I loved being in scenes with him. He had tremendous presence.” — Additional reporting by Kate Ward